Skip to main content

Advertisement

Log in

Applications of Knoevenagel condensation reaction in the total synthesis of natural products

  • Review
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The Knoevenagel condensation reaction is a prominent organic reaction commonly being utilized in the total synthesis of natural and biologically potent products as a vital and frequently beginning step. Naturally occurring compounds having complex structures were demonstrated to exhibit significant biological properties. Due to numerous biological potencies, the total syntheses of them has fascinated and attracted much attention of synthetic organic chemists. In this review, we try to highlight the applications of the Knoevenagel reaction as the key step in the total synthesis of biologically active natural products.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Knoevenagel E (1922) Angew Chem 35:29

    Google Scholar 

  2. Jones G (1967) Org React 15:204

    CAS  Google Scholar 

  3. Knoevenagel E (1898) Ber Dtsch Chem Ges 31:2596

    CAS  Google Scholar 

  4. Knoevenagel E (1894) Ber Dtsch Chem Ges 27:2346

    Google Scholar 

  5. Knoevenagel E (1898) Ber Dtsch Chem Ges 31:2585

    CAS  Google Scholar 

  6. Knoevenagel E, Schmidt E (1894) Ann Chem 281:25

    Google Scholar 

  7. Knoevenagel E, Ruschhaupt W (1898) Ber Dtsch Chem Ges 31:1029

    Google Scholar 

  8. Knoevenagel E (1896) Ber Dtsch Chem Ges 29:172

    CAS  Google Scholar 

  9. Knoevenagel E (1894) Ber Dtsch Chem Ges 27:2345

    Google Scholar 

  10. Freeman F (1980) Chem Rev 80:329

    CAS  Google Scholar 

  11. Tietze LF (1996) Chem Rev 96:115

    CAS  PubMed  Google Scholar 

  12. Tietze LF, Rackelmann N (2004) Pure Appl Chem 76:1967

    CAS  Google Scholar 

  13. Kraus GA, Krolski ME (1986) J Org Chem 51:3347

    CAS  Google Scholar 

  14. Zahouily M, Salah M, Bahlaouane B, Rayadh A, Houmam A, Hamed EA, Sebti S (2004) Tetrahedron 60:1631

    CAS  Google Scholar 

  15. Liang F, Pu YJ, Kurata T, Kido J, Nishide H (2005) Polymer 46:3767

    CAS  Google Scholar 

  16. Lipinska TM (2006) Tetrahedron 62:5736

    CAS  Google Scholar 

  17. Nic M, Jirat J, Kosata B, Jenkins A (1997) IUPAC compendium of chemical terminology, 2nd edn. Blackwell Scientific Publications, Oxford

    Google Scholar 

  18. Manske RHF (1965) The alkaloids: chemistry and physiology, vol 8. Academic Press, New York, p 673

    Google Scholar 

  19. Robbers JE, Speedie MK, Tyler VE (1996) Alkaloids. In: Balado D (ed) Pharmacognosy and pharmacobiotechnology, 9th edn. Lippincott Williams & Wilkins, Philadelphia

  20. Heravi MM, Hamidi H, Zadsirjan V (2014) Curr Org Synth 11:647

    CAS  Google Scholar 

  21. Heravi MM, Lashaki TB, Fattahi B, Zadsirjan V (2018) RSC Adv 8:6634

    CAS  Google Scholar 

  22. Koshvandi ATK, Heravi MM (2018) Appl Organomet Chem 32:3

    Google Scholar 

  23. Heravi MM, Rohani S, Zadsirjan V, Zahedi N (2017) RSC Adv 7:52852

    CAS  Google Scholar 

  24. Heravi MM, Asadi S, Nazari N (2016) Monatsh Chem 147:961

    CAS  Google Scholar 

  25. Heravi MM, Asadi S, Nazari N, Lashkariani BM (2016) Curr Org Synth 13:308

    CAS  Google Scholar 

  26. Heravi MM, Fard MV, Faghihi Z (2015) Curr Org Chem 19:1491

    CAS  Google Scholar 

  27. Heravi MM, Zadsirjan V, Farajpour B (2016) RSC Adv 6:30498

    CAS  Google Scholar 

  28. Heravi MM, Lashaki TB, Poorahmad N (2015) Tetrahedron Asymmetry 26:405

    CAS  Google Scholar 

  29. Heravi MM, Ahmadi T, Ghavidel M (2015) RSC Adv 5:101999

    CAS  Google Scholar 

  30. Heravi MM, Fard MV, Nazari N (2015) Curr Org Chem 19:2358

    CAS  Google Scholar 

  31. Heravi MM, Asadi S, Nazari N (2015) Curr Org Chem 19:2196

    CAS  Google Scholar 

  32. Heravi MM, Vavsari VF (2015) RSC Adv 5:50890

    CAS  Google Scholar 

  33. Heravi MM, Hashemi E, Nazari N (2014) Mol Divers 18:441

    CAS  PubMed  Google Scholar 

  34. Heravi MM, Hashemi E, Azimian F (2014) Tetrahedron 70:7

    CAS  Google Scholar 

  35. Heravi MM, Zadsirjan V, Bozorgpour Savadjani Z (2014) Curr Org Chem 18:2857

    CAS  Google Scholar 

  36. Heravi MM, Bakhtiari A, Faghihi Z (2014) Curr Org Synth 11:787

    CAS  Google Scholar 

  37. Heravi MM, Zadsirjan V (2013) Tetrahedron Asymmetry 24:1149

    CAS  Google Scholar 

  38. Heravi MM, Hashemi E, Ghobadi N (2013) Curr Org Chem 17:2192

    CAS  Google Scholar 

  39. Heravi MM, Hashemi E (2012) Tetrahedron 68:9145

    CAS  Google Scholar 

  40. Kinghorn AD, Farnsworth NR, Soejarto DD, Cordell GA, Pezzuto JM, Udeani GO, Wani MC, Wall ME, Navarro HA, Kramer RA, Menendez AT, Fairchild CR, Lane KE, Forenza S, Vyas DM, Lam KS, Shu YZ (1999) Pure Appl Chem 71:1611

    CAS  Google Scholar 

  41. Marin I, Abad JP, Urena D, Amils R (1995) Biochemistry 34:16519

    CAS  PubMed  Google Scholar 

  42. Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH (1991) J Nat Prod 54:143

    CAS  PubMed  Google Scholar 

  43. Kametani T, Suzuki Y, Ihara M (1979) Can J Chem 57:1679

    CAS  Google Scholar 

  44. Openshaw HT, Robson NC, Whittaker N (1969) J Chem Soc 101

  45. Brauchli P, Deulofeu V, Budzikiewicz H, Djerassi C (1964) J Am Chem Soc 86:1895

    CAS  Google Scholar 

  46. Naito T, Kojima N, Ninomiya I (1986) Chem Pharm Bull 34:3530

    CAS  Google Scholar 

  47. Fujii T, Yoshifuji S (1979) Chem Pharm Bull 27:1486

    CAS  Google Scholar 

  48. Kametani T, Surgenor SA, Fukumoto K (1981) J Chem Soc 920

  49. Ito A, Lee YH, Chai HB, Gupta MP, Farnsforth NR, Gordell GA, Pezzuto JM, Kinghorn AD (1999) J Nat Prod 62:1346

    CAS  PubMed  Google Scholar 

  50. Tietze LF, Bachmann J, Wichmann J, Zhou Y, Raschke T (1997) Liebigs Ann/Recl 1997:881

    Google Scholar 

  51. Tietze LF, Bachmann J, Wichmann J, Burkhardt O (1994) Synthesis 1994:1185

    Google Scholar 

  52. Tietze LF, Zhou Y (1999) Angew Chem Int Ed 38:2045

    CAS  Google Scholar 

  53. Tietze LF, Rackelmann N, Sekar G (2003) Angew Chem Int Ed 42:4254

    CAS  Google Scholar 

  54. Tietze LF, Rackelmann N, Muller I (2004) Chem Eur J 10:2722

    CAS  PubMed  Google Scholar 

  55. Farmer RL, Biddle MM, Nibbs AE, Huang XK, Bergan RC, Scheidt KA (2010) ACS Med Chem Lett 1:400

    CAS  PubMed  PubMed Central  Google Scholar 

  56. Biddle MM, Lin M, Scheidt KA (2007) J Am Chem Soc 129:3830

    CAS  PubMed  Google Scholar 

  57. Custar DW, Zabawa TP, Scheidt KA (2008) J Am Chem Soc 130:804

    CAS  PubMed  Google Scholar 

  58. Snider BB, Kwon T (1992) J Org Chem 57:2399

    CAS  Google Scholar 

  59. Rebecca L, Farmer A, Scheidt K (2013) Chem Sci 4:3304

    Google Scholar 

  60. Morita H, Hirasawa Y, Shinzato T, Kobayashi J (2004) Tetrahedron 60:7015

    CAS  Google Scholar 

  61. Morita H, Hirasawa Y, Yoshida N, Kobayashi J (2001) Tetrahedron Lett 42:4199

    CAS  Google Scholar 

  62. Hirasawa Y, Morita H, Kobayashi J (2003) Tetrahedron 59:3567

    CAS  Google Scholar 

  63. Hirasawa Y, Morita H, Kobayashi J (2004) Heterocycles 64:515

    CAS  Google Scholar 

  64. Ma X, Gang DR (2004) Nat Prod Rep 21:752

    CAS  PubMed  Google Scholar 

  65. Snider BB, Grabowski JF (2007) J Org Chem 72:1039

    CAS  PubMed  PubMed Central  Google Scholar 

  66. Michael JP (2007) Nat Prod Rep 24:191

    CAS  PubMed  Google Scholar 

  67. Ohmiya S, Saito K, Murakoshi I (1995) Lupine alkaloids. In: Cordell GA (ed) The alkaloids: chemistry and pharmacology, 47th edn. Academic Press, New York

    Google Scholar 

  68. Leonard NJ (1953) Lupin alkaloids. In: Manske RHF, Holmes HL (eds) The alkaloids: chemistry and physiology, 3rd edn. Academic Press, New York

    Google Scholar 

  69. Leonard NJ (1960) Lupin alkaloids. In: Manske RHF (ed) The alkaloids: chemistry and physiology, 7th edn. Academic Press, New York

    Google Scholar 

  70. Norcross NR, Melbardis JP, Solera MF, Sephton MA, Kilner C, Zakharov LN, Astles PC, Warriner SL, Blakemore PR (2008) J Org Chem 73:7939

    CAS  PubMed  Google Scholar 

  71. Aoki S, Watanabe Y, Sanagawa M, Setiawan A, Kotoku N, Kobayashi M (2006) J Am Chem Soc 128:3148

    CAS  PubMed  Google Scholar 

  72. Watanabe Y, Aoki S, Tanabe D, Setiawan A, Kobayashi M (2007) Tetrahedron 63:4074

    CAS  Google Scholar 

  73. Yamashita S, Iso K, Kitajima K, Himuro M, Hirama M (2011) J Org Chem 76:2408

    CAS  PubMed  Google Scholar 

  74. Liu ZJ, Lu R (1988) Gelsemium alkaloids. In: Brossi A (ed) The alkaloids: chemistry and pharmacology, 33rd edn. Academic Press, New York

    Google Scholar 

  75. Saxton JE (1965) Alkaloids of gelsemium species. In: Manske RHF (ed) The alkaloids: chemistry and physiology, 8th edn. Academic Press, New York

    Google Scholar 

  76. Lovell L, Pepinsky R, Wilson AJC (1959) Tetrahedron Lett 4:1

    Google Scholar 

  77. Conroy H, Chakrabarti JK (1959) Tetrahedron Lett 4:6

    Google Scholar 

  78. Kondo K, Umemoto T, Yako K, Tunemoto D (1978) Tetrahedron Lett 19:3927

    Google Scholar 

  79. Fukuyama T, Liu G (1996) J Am Chem Soc 118:7426

    CAS  Google Scholar 

  80. Nakano H, Matsuda Y, Ito K, Ohkubo S, Morimoto M, Tomita F (1981) J Antibiot 34:266

    CAS  PubMed  Google Scholar 

  81. Balitz DM, O’Herron FA, Bush J, Vyas DM, Nettleton DE, Grulich RE, Bradner WT, Doyle TW, Arnold E, Clardy J (1981) J Antibiot 34:1544

    CAS  PubMed  Google Scholar 

  82. Takahashi K, Yoshida M, Tomita F, Shirahata K (1981) J Antibiot 34:271

    CAS  PubMed  Google Scholar 

  83. Hirayama N, Takahashi K, Shirahata K, Ohashi Y, Sasada Y (1981) Bull Chem Soc Jpn 54:1338

    CAS  Google Scholar 

  84. Mishra R, Tritch HR, Pandey RC (1985) J Antibiot 38:1280

    Google Scholar 

  85. Tse-Dinh TC, McGee LR (1987) Biochem Biophys Res Commun 143:808

    CAS  PubMed  Google Scholar 

  86. Tomito F, Takahashi KI, Tamaoki T (1982) J Antibiot 35:1038

    Google Scholar 

  87. Elespuru RK, Gonda SK (1984) Science 223:69

    CAS  PubMed  Google Scholar 

  88. McGee LR, Mishra R (1990) J Am Chem Soc 112:2386

    CAS  Google Scholar 

  89. Morimoto M, Okubo S, Tomito F, Marumo H (1981) J Antibiot 34:701

    CAS  PubMed  Google Scholar 

  90. Matsumoto A, Fujiwara Y, Elespuru RK, Hanawalt PC (1994) Photochem Photobiol 60:225

    CAS  PubMed  Google Scholar 

  91. Reddy P, Nandaluru J, Bodwell J (2012) Org Chem 77:8028

    Google Scholar 

  92. TePaske MR, Gloer JB, Wicklow DT, Dowd PF (1991) Tetrahedron Lett 32:5687

    CAS  Google Scholar 

  93. Tietze LF, Geissler H, Fennen J, Brumby T, Brand S, Schulz G (1994) J Org Chem 59:182

    CAS  Google Scholar 

  94. Teitze LF, Beifuss U (1993) Angew Chem Int Ed 32:131

    Google Scholar 

  95. Tietze LF (1990) J Heterocycl Chem 27:47

    CAS  Google Scholar 

  96. Matlin SA, Sammes PG, Upton RM (1979) J Chem Soc 2481

  97. Rigby JH, Qabar M (1989) J Org Chem 54:5852

    CAS  Google Scholar 

  98. Snider BB, Lu Q (1996) J Org Chem 61:2839

    CAS  PubMed  Google Scholar 

  99. Kakeya H, Kageyama S, Nie L, Onose R, Okada G, Beppu T, Norbury CJ, Osada H (2001) J Antibiot 54:850

    CAS  PubMed  Google Scholar 

  100. Kakeya H, Takahashi I, Okada G, Isono K, Osada H (1995) J Antibiot 48:733

    CAS  PubMed  Google Scholar 

  101. Hayashi Y, Kanayama J, Yamaguchi J, Shoji M (2002) J Org Chem 67:9443

    CAS  PubMed  Google Scholar 

  102. Brady SF, Singh MP, Janso JE, Clardy J (2000) J Am Chem Soc 122:2116

    CAS  Google Scholar 

  103. Singh MP, Janso JE, Luckman SW, Brady SF, Clardy J, Greenstein M, Maiese WM (2000) J Antibiot 53:256

    CAS  PubMed  Google Scholar 

  104. Brady SF, Bondi SM, Clardy J (2001) J Am Chem Soc 123:9900

    CAS  PubMed  Google Scholar 

  105. Mandal M, Yun H, Dudley GB, Lin S, Tan DS, Danishefsky SJ (2005) J Org Chem 70:10619

    CAS  PubMed  Google Scholar 

  106. Gan C-Y, Low Y-Y, Etoh T, Hayashi M, Komiyama K, Kam T-S (2009) J Nat Prod 72:2098

    CAS  PubMed  Google Scholar 

  107. Basha A, Lipton M, Weinreb SM (1977) Tetrahedron Lett 18:4171

    Google Scholar 

  108. Sirasani G, Andrade RB (2011) Org Lett 13:17

    Google Scholar 

  109. Johnson G, Sunderwirth SG, Gibian H, Coulter AW, Gassner FX (1963) Phytochemistry 2:145

    CAS  Google Scholar 

  110. Kelley CJ, Harruff RC, Carmack M (1976) J Org Chem 41:449

    CAS  Google Scholar 

  111. Kelley CJ, Mahajan JR, Brooks LC, Neubert LA, Breneman WR, Carmack M (1975) J Org Chem 40:1804

    CAS  Google Scholar 

  112. Wagner H, Whittmann D, Schafer W (1975) Tetrahedron Lett 16:547

    Google Scholar 

  113. Chen L, Wang W-Y, Wang Y-P (2009) Acta Pharm Sin 30:1245

    CAS  Google Scholar 

  114. Ghosh AK, Cheng X, Zhou B (2012) Org Lett 14:19

    Google Scholar 

  115. Gürtler H, Pedersen R, Anthoni U, Christophersen C, Nielsen PH, Wellington EMH, Pedersen C, Bock K (1994) J Antibiot 47:434

    PubMed  Google Scholar 

  116. Kobayashi T, Kon Y, Abe H, Ito H (2014) Org Lett 16:6397

    CAS  PubMed  Google Scholar 

  117. Brown LE, Cheng KC-C, Wei WG, Yuan PW, Dai P, Trilles R, Ni F, Yuan J, MacArthur R, Guha R, Johnson RL, Su XZ, Dominguez MM, Snyder JK, Beeler AB, Schaus SE, Inglese J, Porco JA (2011) Proc Natl Acad Sci USA 108:6775

    CAS  PubMed  Google Scholar 

  118. Reckendorf WM (1966) Angew Chem Int Ed 5:665

    Google Scholar 

  119. Shibuya M, Jaisli F, Eschenmoser A (1979) Angew Chem Int Ed 18:636

    Google Scholar 

  120. Bohlmann F, Jakupovic J, Misra LN, Castro V (1985) Liebigs Ann Chem 1985:1367

    Google Scholar 

  121. Herath HMTB, Priyadarshani AMA, Jamie J (1998) Nat Prod Lett 12:91

    CAS  Google Scholar 

  122. Ferris GE, Hong K, Roundtree IA, Morken JP (2013) J Am Chem Soc 135:2501

    CAS  PubMed  PubMed Central  Google Scholar 

  123. Wanner MJ, Boots RNA, Eradus B, Gelder RD, van Maarseveen JH, Hiemstra H (2009) Org Lett 11:2579

    CAS  PubMed  Google Scholar 

  124. Reyes E, Talavera G, Vicario JL, Badía D, Carrillo L (2009) Angew Chem Int Ed 48:5701

    CAS  Google Scholar 

  125. Michrowska A, List B (2009) Nat Chem 1:225

    CAS  PubMed  Google Scholar 

  126. Jones SB, Simmons B, Mastracchio A, MacMillan DWC (2011) Nature 475:183

    CAS  PubMed  PubMed Central  Google Scholar 

  127. Tan H, Chen X, Chen H, Liu H, Qiu S (2015) Eur J Org Chem 2015:4956

    CAS  Google Scholar 

  128. Herath HMTB, Padmasiri W (1999) Nat Prod Lett 14:141

    CAS  Google Scholar 

  129. Herath HMTB, Priyadarshani AMA, Jamie J (1996) Phytochemistry 42:1439

    CAS  Google Scholar 

  130. Herath HMTB, Priyadarshani AMA, Jamie J (1997) Phytochemistry 44:699

    CAS  Google Scholar 

  131. Tan H, Liu H, Chen X, Chen H, Qiu S (2015) Org Biomol Chem 13:9977

    CAS  PubMed  Google Scholar 

  132. Wang W, Kim H, Nam S-J, Rho BJ, Kang H (2012) J Nat Prod 75:2049

    CAS  PubMed  Google Scholar 

  133. Won TH, Jeon J-E, Kim S-H, Lee S-H, Rho BJ, Oh D-C, Oh K-B, Shin J (2012) J Nat Prod 75:2055

    CAS  PubMed  Google Scholar 

  134. Liang J, Hu W, Tao P, Jia Y (2013) J Org Chem 78:5810

    CAS  PubMed  Google Scholar 

  135. Roy S, Davydova MP, Pal R, Gilmore K, Tolstikov GA, Vasilevsky SF, Alabugin IV (2011) J Org Chem 76:7482

    CAS  PubMed  Google Scholar 

  136. Boukouvalas J, Thibault C (2015) J Org Chem 80:681

    CAS  PubMed  Google Scholar 

  137. Quinoa K, Crews PP (1987) Tetrahedron Lett 28:3229

    CAS  Google Scholar 

  138. Rodriguez AD, Akee RK, Scheuer PJ (1987) Tetrahedron Lett 28:4989

    CAS  Google Scholar 

  139. Arabshahi L, Schmitz FJ (1987) J Org Chem 52:3584

    CAS  Google Scholar 

  140. Kim D, Lee IS, Jung JH, Yang S-I (1999) Arch Pharm Res 22:25

    CAS  PubMed  Google Scholar 

  141. Kim D, Lee IS, Jung JH, Lee CO, Choi SU (1999) Anticancer Res 19:4085

    CAS  PubMed  Google Scholar 

  142. Jung JH, Sim CJ, Lee CO (1995) J Nat Prod 58:1722

    CAS  PubMed  Google Scholar 

  143. Pin IC, Gautschi JC, Wang GYS, Sanders ML, Schmitz FJ, France D, Cornell-Kennon S, Sambucetti LC, Remiszewski SW, Perez LB, Bair KW, Crews J (2003) Org Chem 38:3688

    Google Scholar 

  144. Shin J, Lee H-S, Seo Y, Rho JR, Cho KW, Paul VJ (2000) Tetrahedron 56:9071

    CAS  Google Scholar 

  145. Mora FD, Jones DK, Desai PV, Patny A, Avery MA, Feller DR, Smillie T, Zhou Y-D, Nagle DG (2006) J Nat Prod 69:547

    CAS  PubMed  Google Scholar 

  146. Hong S, Lee M, Jung M, Park Y, Kim M-H, Park H-G (2012) Tetrahedron Lett 53:4209

    CAS  Google Scholar 

  147. Miao S, Andersen RJ (1991) J Org Chem 56:6275

    CAS  Google Scholar 

  148. Ortega MJ, Zubia E, Ocana JM, Naranjo S, Salva J (2000) Tetrahedron 56:3963

    CAS  Google Scholar 

  149. Kotora M, Negishi E (1997) Synthesis 1997:121

    Google Scholar 

  150. Boukouvalas J, Lachance N, Ouellet M, Trudeau M (1998) Tetrahedron Lett 39:7665

    CAS  Google Scholar 

  151. Prim D, Fuss A, Krisch G, Silva AMS (1999) J Chem Soc Perkin Trans 1175

  152. Chavan SP, Pathak AB, Pandey A, Kalkote UR (2007) Synth Commun 37:4253

    CAS  Google Scholar 

  153. Chen YS, Lee SM, Lin YJ, Chiang SH, Lin ChCh (2014) Molecules 19:2029

    PubMed  PubMed Central  Google Scholar 

  154. Wang BQ (2010) J Med Plants Res 4:2813

    CAS  Google Scholar 

  155. Lam FFY, Yeung JHK, Chan KM, Or PMY (2007) Vasc Pharmacol 46:271

    CAS  Google Scholar 

  156. Shen Y, Hu Y, Zhang Y (2011) Hypertens Pregnancy 30:465

    CAS  PubMed  Google Scholar 

  157. Sidoryk K, Filip K, Cmoch P, Laszcz M, Cybulski M (2018) J Mol Struct 1153:135

    CAS  Google Scholar 

  158. Li XL, Xu MJ, Zhao YL, Xu J (2010) Molecules 15:9298

    CAS  PubMed  PubMed Central  Google Scholar 

  159. Campaigne E, Hutchinson JH (1970) J Heterocycl Chem 7:655

    CAS  Google Scholar 

  160. Lawson W, Perkin WH, Robinson R (1924) J Chem Soc 125:626

    CAS  Google Scholar 

  161. Godard A, Queguiner G (1980) J Heterocycl Chem 17:465

    CAS  Google Scholar 

  162. Tian C, Jiao X, Liu X, Li R, Dong L, Liu X, Zhang Z, Xu J, Xu M, Xie P (2012) Tetrahedron Lett 53:4892

    CAS  Google Scholar 

  163. ElSohly MA, Slade D (2005) Life Sci 78:539

    CAS  PubMed  Google Scholar 

  164. Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, Bonner TI (1990) Nature 365:61

    Google Scholar 

  165. Munro S, Thomas KL, Abu-Shaar M (1993) Nature 365:61

    CAS  PubMed  Google Scholar 

  166. Marriot KS, Huffman JW (2008) Curr Top Med Chem 8:187

    Google Scholar 

  167. Pertwee RG (1997) Pharmacol Ther 74:129

    CAS  PubMed  Google Scholar 

  168. Nandaluru PR, Bodwell GJ (2012) Org Lett 14:1

    Google Scholar 

  169. Baeckstrom P, Sundstrom G (1970) Acta Chem Scand 24:716

    CAS  Google Scholar 

  170. Torang J, Nieger M, Brase S (2005) Synthesis 2005:1888

    Google Scholar 

  171. Saleem M, Hussain H, Ahmed I, van Reec T, Krohn K (2011) Nat Prod Rep 28:1534

    CAS  PubMed  Google Scholar 

  172. Chen DYK (2011) Synlett 2011:2459

    Google Scholar 

  173. Tiefenbacher K, Mulzer J (2008) Angew Chem Int Ed 47:2548

    CAS  Google Scholar 

  174. Wang Z (2012) Synlett 23:2311

    CAS  Google Scholar 

  175. Gao P, Hou TP, Gao R, Cui Q, Liu SG (2001) Pest Manag Sci 57:307

    CAS  PubMed  Google Scholar 

  176. Kogiso SM, Hosozawa S, Wada K, Munakata K (1974) Phytochemistry 13:2332

    CAS  Google Scholar 

  177. Xu G, Yang X, Jiang B, Lei P, Liu X, Wang Q, Zhang X, Ling Y (2016) Bioorg Med Chem Lett 26:1849

    CAS  PubMed  Google Scholar 

  178. Ward RS (1999) Nat Prod Rep 16:75

    CAS  Google Scholar 

  179. Lee S, Yoo HH, Piao XL, Kim JS, Kang SS, Shin KH (2005) Arch Pharm Res 28:186

    CAS  PubMed  Google Scholar 

  180. Janmanchi D, Lin CH, Hsieh J-Y, Tseng Y-P, Chen T-A, Jhuang H-J, Yeh SF (2013) Bioorg Med Chem 21:2163

    CAS  PubMed  Google Scholar 

  181. Hajdu Z, Haskó J, Krizbai IA, Wilhelm I, Jedlinszki N, Fazakas C, Molnár J, Forgo P, Hohmann J, Csupor D (2014) J Nat Prod 77:2641

    CAS  PubMed  Google Scholar 

  182. Kao T-T, Lin C-C, Shia K-S (2015) J Org Chem 80:6708

    CAS  PubMed  Google Scholar 

  183. Clifford MN, Marks S, Knight S, Kuhnert N (2006) J Agric Food Chem 54:4095

    CAS  PubMed  Google Scholar 

  184. Robinson WE Jr, Reinecke MG, Abdel-Malek S, Chow SA (1996) Proc Natl Acad Sci USA 93:6326

    CAS  PubMed  Google Scholar 

  185. Tamura H, Akioka T, Ueno K, Chujyo T, Okazaki K-I, King PJ, Robinsion WE (2006) Mol Nutr Food Res 50:396

    CAS  PubMed  Google Scholar 

  186. Ojwang JO, Wang Y-H, Wyde PR, Fischer NH, Schuehly W, Appleman JR, Hinds S, Shimasaki CD (2005) Antiviral Res 68:163

    CAS  PubMed  Google Scholar 

  187. Antonio AG, Moraes RS, Perrone D, Maia LC, Santos KN, Lurio NLP, Farah A (2010) Food Chem 118:782

    CAS  Google Scholar 

  188. Raheem KS, Botting NP, Williamson G, Barron D (2011) Tetrahedron Lett 52:7175

    CAS  Google Scholar 

  189. Dao TT, Tran TL, Kim J, Nguyen PH, Lee EH, Park J, Jang IS, Oh WK (2012) J Nat Prod 75:1332

    CAS  PubMed  Google Scholar 

  190. Bigi F, Carloni S, Ferrari L, Maggi R, Mazzacani A, Sartori G (2001) Tetrahedron Lett 42:5203

    CAS  Google Scholar 

  191. Silva AC, Benelkebir H, Lopes RSC, Lopesa CC, Ganesan A (2018) J Braz Chem Soc 29:1157

    CAS  Google Scholar 

  192. Sun Y, Tian L, Huang J, Ma H-Y, Zheng Z, Lv A-L, Yasukawa K, Pei Y-H (2008) Org Lett 10:393

    CAS  PubMed  Google Scholar 

  193. Myers E, Herrero-Gómez E, Baitinger I, Lachs J, Mayer P, Hanni M, Ochsenfeld C, Trauner D (2014) J Org Chem 79:9812

    CAS  PubMed  Google Scholar 

  194. Harrity JPA, Provoost O (2005) Org Biomol Chem 3:1349

    CAS  PubMed  Google Scholar 

  195. Hsung RP, Kurdyumov AV, Sydorenko N (2005) Eur J Org Chem 2005:23

    Google Scholar 

  196. Deng J, Wang X-N, Hsung RP (2014) A formal [3+3] cycloaddition approach to natural product synthesis. In: Nishiwaki N (ed) Methods and applications of cycloaddition reactions in organic syntheses, 12th edn. Wiley-VCH, Weinheim

    Google Scholar 

  197. Xu X, Doyle MP (2014) Acc Chem Res 47:1396

    CAS  PubMed  PubMed Central  Google Scholar 

  198. Moyano A, Rios R (2011) Chem Rev 111:4703

    CAS  PubMed  Google Scholar 

  199. Fotiadou D, Zografos AL (2012) Org Lett 14:5664

    CAS  PubMed  Google Scholar 

  200. Hu J, Dong W, Wu X-Y, Tong X (2012) Org Lett 14:5530

    CAS  PubMed  Google Scholar 

  201. Bulger PG, Bagal SK, Marquez R (2008) Nat Prod Rep 25:254

    CAS  PubMed  Google Scholar 

  202. Luoa G-Y, Wua H, Tang Y, Lia H, Yeomb H-S, Yanga K, Hsung RP (2015) Synthesis 47:2713

    Google Scholar 

  203. Murrayamine M, Wu T-S, Wang M-L, Wu P-L, Ito C, Furukawa H (1996) Phytochemistry 41:1433

    Google Scholar 

  204. Duffield AM, Jefferies PR, Maslen FN, Roe AM (1963) Tetrahedron 19:593

    CAS  Google Scholar 

  205. Crombie L, Redshaw SD, Black DA, Whiting DA (1979) J Chem Soc Chem Commun 628

  206. Crombie L, Redshaw SD, Black DA, Whiting DA (1983) J Chem Soc Perkin Trans 1:1411

    Google Scholar 

  207. Yuan W, Cheng S, Fu W, Zhao M, Li X, Cai Y, Dong J, Huang K, Gustafson KR, Yan P (2016) J Nat Prod 79:1124

    CAS  PubMed  PubMed Central  Google Scholar 

  208. Cheng S-Y, Huang K-J, Wang S-K, Wen Z-H, Chen P-W, Duh C-Y (2010) J Nat Prod 73:771

    CAS  PubMed  Google Scholar 

  209. Lam HC, Pepper HP, Sumby CJ, George JH (2017) Angew Chem Int Ed 56:1

    Google Scholar 

  210. Xu J, Lacoske MH, Theodorakis EA (2014) Angew Chem Int Ed 53:956

    CAS  Google Scholar 

  211. Akagi M, Matsui N, Akae H, Hirashima N, Fukuishi N, Fukuyama Y, Akagi R (2015) J Pharmacol Sci 127:155

    CAS  PubMed  Google Scholar 

  212. Carcache DA, Cho YS, Hua Z, Tian Y, Li Y-M, Danishefsky SJ (2006) J Am Chem Soc 128:1016

    CAS  PubMed  Google Scholar 

  213. Trzoss L, Xu J, Lacoske MH, Mobley WC, Theodorakis EA (2013) Chem Eur J 19:6398

    CAS  PubMed  Google Scholar 

  214. Wolinsky J, Chan D (1965) J Org Chem 30:41

    CAS  Google Scholar 

  215. Marx JN, Norman LR (1975) J Org Chem 40:1602

    CAS  Google Scholar 

  216. Gomes J, Daeppen C, Liffert R, Roesslein J, Kaufmann E, Heikinheimo A, Neuburger M, Gademann K (2016) J Org Chem 81:11017

    CAS  PubMed  Google Scholar 

  217. Bauer I, Knölker H-J (2012) Top Curr Chem 309:203

    CAS  PubMed  Google Scholar 

  218. Schmidt AW, Reddy KR, Knölker H-J (2012) Chem Rev 112:3193

    CAS  PubMed  Google Scholar 

  219. Hesse R, Gruner KK, Kataeva O, Schmidt AW, Knölker H-J (2013) Chem Eur J 19:14098

    CAS  PubMed  Google Scholar 

  220. Dai J, Ma D, Fu C, Ma S (2015) Eur J Org Chem 2015:5655

    CAS  Google Scholar 

  221. Singh IP, Bharate SB (2006) Nat Prod Rep 23:558

    CAS  Google Scholar 

  222. Chen J, Craven LA (2007) Flora of China, vol 13. Science Press/Missouri Botanical Garden Press, Beijing, p 330

    Google Scholar 

  223. Lavanya G, Voravuthikunchai SP, Towatana NH (2012) J Evid Based Complement Altern Med 2012:535479

    Google Scholar 

  224. Liu H-X, Zhang WM, Xu Z-F, Chen Y-C, Tan H-B, Qiu S-X (2016) RSC Adv 6:25882

    CAS  Google Scholar 

  225. Liu H-X, Chen K, Tang G-H, Yuan Y-F, Tan H-B, Qiu S-X (2016) RSC Adv 6:25882

    CAS  Google Scholar 

  226. Chen T, Yu CG, Yang BL (2011) Chem Nat Compd 47:524

    Google Scholar 

  227. Joab D, Han S (2017) Org Chem Front 4:506

    Google Scholar 

  228. Zou Y, Xu W, Tsunematsu Y, Tang M, Watanabe K, Tang Y (2014) Org Lett 16:6390

    CAS  PubMed  PubMed Central  Google Scholar 

  229. Stierle AA, Stierle DB, Patacini B (2008) J Nat Prod 71:856

    CAS  PubMed  Google Scholar 

  230. Wiemann P, Guo CJ, Palmer JM, Sekonyela R, Wang CCC, Keller NP (2013) Proc Natl Acad Sci USA 110:17065

    CAS  PubMed  Google Scholar 

  231. Tsunematsu Y, Fukutomi M, Saruwatari T, Noguchi H, Hotta K, Tang Y, Watanabe K (2014) Angew Chem Int Ed 53:8475

    CAS  Google Scholar 

  232. Asami Y, Kakeya H, Onose R, Yoshida A, Matsuzaki H, Osada H (2002) Org Lett 4:2845

    CAS  PubMed  Google Scholar 

  233. Asami Y, Kakeya H, Komi Y, Kojima S, Nishikawa K, Beebe K, Neckers L, Osada H (2008) Cancer Sci 99:1853

    CAS  PubMed  PubMed Central  Google Scholar 

  234. Carbone M, Nunez-Pons L, Castellucccio F, Avila C, Gavagnin M (2009) J Nat Prod 72:1357

    CAS  PubMed  Google Scholar 

  235. Palermo JA, Rodriguez Brasco MF, Spagnuolo C, Seldes AM (2000) J Org Chem 65:4482

    CAS  PubMed  Google Scholar 

  236. Castillo UF, Sakagami Y, Alonso-Amelot M, Ojika M (1999) Tetrahedron 55:12295

    CAS  Google Scholar 

  237. Finkielsztein LM, Bruno AM, Renou SG, Iglesias GY (2006) Bioorg Med Chem 14:1863

    CAS  PubMed  Google Scholar 

  238. Pettit GR, Meng Y, Pettit RK, Herald DL, Cichacz ZA, Doubek DL, Richert L (2010) J Nat Prod 73:388

    CAS  PubMed  PubMed Central  Google Scholar 

  239. Suresh M, Kumar N, Veeraraghavaiah G, Hazra S, Singh RB (2016) J Nat Prod 79:2740

    CAS  PubMed  Google Scholar 

  240. Roethle PA, Trauner D (2008) Nat Prod Rep 25:298

    CAS  PubMed  Google Scholar 

  241. Li Y, Pattenden G (2011) Nat Prod Rep 28:1269

    CAS  PubMed  Google Scholar 

  242. Missakian MG, Burresons BJ, Scheuer PJ (1975) Tetrahedron 31:2513

    CAS  Google Scholar 

  243. Fenical W, Okuda RK, Banduragga MM, Culver P, Jacobs RS (1981) Science 212:1512

    CAS  PubMed  Google Scholar 

  244. Tang B, Bray CD, Pattenden G (2009) Org Biomol Chem 7:4448

    CAS  PubMed  Google Scholar 

  245. Tang B, Bray CD, Pattenden G, Rogers J (2010) Tetrahedron 66:2492

    CAS  Google Scholar 

  246. McAulay K, Clark JS (2017) Chem Eur J 23:9761

    CAS  PubMed  Google Scholar 

  247. Hu L-Z, Zhang Y, Zhu H-C (2016) Org Lett 18:2272

    CAS  PubMed  Google Scholar 

  248. Li C-J, Ma J, Sun H, Zhang D, Zhang D-M (2016) Org Lett 18:168

    CAS  PubMed  Google Scholar 

  249. Cottiglia F, Casu L, Leont M (2012) J Nat Prod 75:225

    CAS  PubMed  Google Scholar 

  250. Zhou W-L, Tan H-B, Qiu S-X, Chen G-Y, Liu H-X, Zheng C (2017) Tetrahedron Lett 58:1817

    CAS  Google Scholar 

  251. Schroeder FC, Kau TR, Silver PA, Clardy J (2005) J Nat Prod 68:574

    CAS  PubMed  Google Scholar 

  252. Gribble GW (2012) Occurrence of halogenated alkaloids. In: Knölker HJ (ed) The alkaloids: chemistry and biology, 71st edn. Academic Press, New York

    Google Scholar 

  253. Boccitto M, Lee N, Sakamoto S, Spruce LA, Handa H, Clardy J, Seeholzer SH, Kalb RG (2017) Mar Drugs 15:246

    PubMed Central  Google Scholar 

  254. Xu J, Wanga K, Wu J (2018) RSC Adv 8:13747

    CAS  Google Scholar 

  255. Welch WM, Kraska AR, Sarges R, Koe BK (1984) J Med Chem 27:1508

    CAS  PubMed  Google Scholar 

  256. Lowe JA III, Hageman DL, Drozda SE, Mclean S, Bryce DK, Crawford RT, Zorn S, Morrone J, Bordner J (1994) J Med Chem 37:3789

    CAS  PubMed  Google Scholar 

  257. Bogeso KP, Christensen AV, Hyttel J, Liljefors T (1985) J Med Chem 28:1817

    CAS  PubMed  Google Scholar 

  258. Lee BH, Choi YL, Shin S, Heo JN (2011) J Org Chem 76:6611

    CAS  PubMed  Google Scholar 

  259. Ryabukhin SV, Plaskon AS, Volochnyuk DM, Pipko SE, Shivanyuk AN, Tolmachev AA (2007) J Comb Chem 9:1073

    CAS  PubMed  Google Scholar 

  260. Drago C, Caggiano L, Jackson RF (2005) Angew Chem Int Ed 44:7221

    CAS  Google Scholar 

  261. Tang M-L, Peng P, Liu Z-Y, Zhang J, Yu J-M, Sun X (2016) Chem Eur J 22:14535

    PubMed  Google Scholar 

  262. Kobayashi J, Kubota T (2009) Nat Prod Rep 26:936

    CAS  PubMed  Google Scholar 

  263. Chattopadhyay AK, Hanessian S (2017) Chem Rev 117:4104

    CAS  PubMed  Google Scholar 

  264. Zhang H, Zhang D-D, Li J-Y, Shyaula SL, Li J, Yue J-M (2016) RSC Adv 6:44402

    CAS  Google Scholar 

  265. Lopez AM, Ibrahim AA, Rosenhauer GJ, Sirinimal HS, Stockdil L (2018) Org Lett 20:2216

    CAS  PubMed  PubMed Central  Google Scholar 

  266. Dalessandro EV, Collin HP, Guimarães LGL, Valle MS, Pliego JR (2017) J Phys Chem B 121:5300

    CAS  PubMed  Google Scholar 

  267. Hamlin AM, Kisunzu JK, Sarpong R (2014) Org Biomol Chem 12:1846

    CAS  PubMed  Google Scholar 

  268. Liu X-Y, Qin Y (2015) Asian J Org Chem 4:1010

    CAS  Google Scholar 

  269. Zhu G, Liu R, Liu B (2015) Synthesis (Mass) 47:2691

    CAS  Google Scholar 

  270. Chen K, Baran PS (2009) Nature 459:824

    CAS  PubMed  Google Scholar 

  271. Wang F-P, Chen Q-H, Liu X-Y (2010) Nat Prod Rep 27:529

    CAS  PubMed  Google Scholar 

  272. Gong CH, Liu X-Y, Wang Z-X, Nie W, Qin Y (2016) Nat Commun 7:12183

    CAS  PubMed  PubMed Central  Google Scholar 

  273. Maslovskaya LA, Savchenko AI, Krenske EH, Gordon VA, Reddell PW, Pierce CJ, Parsons PG, Williams CM (2014) Chem Comm 50:12315

    CAS  PubMed  Google Scholar 

  274. Zhang XL, Wang L, Li F, Yu K, Wang MK (2013) J Nat Prod 76:858

    CAS  PubMed  Google Scholar 

  275. Hanson JR (2012) Nat Prod Rep 29:890

    CAS  PubMed  Google Scholar 

  276. Hanson JR (2013) Nat Prod Rep 30:1346

    CAS  PubMed  Google Scholar 

  277. Thombal RS, Jadhav VH (2015) Org Biomol Chem 13:9485

    CAS  PubMed  Google Scholar 

  278. Nair MSR, Takeshita H, McMorris TC, Anchel M (1969) J Org Chem 34:240

    CAS  PubMed  Google Scholar 

  279. Woodward RB, Hoye TR (1977) J Am Chem Soc 99:8007

    CAS  Google Scholar 

  280. Morrison AE, Hoang TT, Birepinte M, Dudley GB (2017) Org Lett 19:858

    CAS  PubMed  Google Scholar 

  281. Wu Z-L, Zhao B-X, Huang X-J, Tang G-Y, Shi L, Jiang R-W, Liu X, Wang Y, Ye W-C (2014) Angew Chem Int Ed 53:5796

    CAS  Google Scholar 

  282. Wiest JM, Bach T (2016) J Org Chem 81:6149

    CAS  PubMed  Google Scholar 

  283. Rutkowski J, Brzezinski B (2013) Biomed Res Int 2013:162513

    PubMed  PubMed Central  Google Scholar 

  284. Wang B-G, Gloer JB, Ji N-Y, Zhao J-C (2013) Chem Rev 113:3632

    CAS  PubMed  Google Scholar 

  285. Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR (2013) Nat Prod Rep 30:237

    CAS  PubMed  Google Scholar 

  286. Kurosawa E, Fukuzawa A, Irie T (1972) Tetrahedron Lett 21:2121

    Google Scholar 

  287. Suzuki T, Koizumi K, Suzuki M, Kurosawa E (1983) Chem Lett 12:1643

    Google Scholar 

  288. Martín T, Padrón JI, Martín VS (2014) Synlett 25:12

    Google Scholar 

  289. Li E, Jiang L, Guo L, Zhang H, Che Y (2008) Bioorg Med Chem 16:7894

    CAS  PubMed  Google Scholar 

  290. Zask A, Ellestad G (2018) Chirality 30:157

    CAS  PubMed  Google Scholar 

  291. Wei M-Y, Li D, Shao C-L, Deng D-S, Wang C-Y (2013) Mar Drugs 11:1050

    CAS  PubMed  PubMed Central  Google Scholar 

  292. Arredondo V, Roa DE, Yan S, Liu-Smith F, Van Vranken DL (2019) Org Lett 21:1755

    CAS  PubMed  Google Scholar 

  293. Wang FP, Chen QH (2010) The C19-diterpenoid alkaloids. In: Cordell GA (ed) The alkaloids: chemistry and biology, 69th edn. Elsevier Science, New York

    Google Scholar 

  294. Tashkhodzhaev B, Saidkhodzhaeva SA, Bessonova IA, Antipin MY (2000) Chem Nat Compd 36:79

    CAS  Google Scholar 

  295. Nie W, Gong J, Chen Z, Liu J, Tian D, Song H, Liu X-Y, Qin Y (2019) J Am Chem Soc 141:9712

    CAS  PubMed  Google Scholar 

  296. O’Connor SE, Maresh JJ (2006) Nat Prod Rep 23:532

    PubMed  Google Scholar 

  297. Szabó LF (2008) Molecules 13:1875

    PubMed  PubMed Central  Google Scholar 

  298. Lémus C, Kritsanida M, Canet A, Genta-Jouve G, Michel S, Deguin B, Grougnet R (2015) Tetrahedron Lett 56:5377

    Google Scholar 

  299. Li L, Yuan K, Jia Q, Jia Y (2019) Angew Chem Int Ed 58:6074

    CAS  Google Scholar 

  300. Douki K, Shimokawa J, Kitamura M (2019) Org Biomol Chem 17:1727

    CAS  PubMed  Google Scholar 

  301. Dou Y, Kouklovsky C, Gandon V, Vincent G (2019) Angew Chem Int Ed 59:1527

    Google Scholar 

  302. Cheng MJ, Cao JQ, Yang XY, Zhong LP, Hu LJ, Lu X, Hou BL, Hu YJ, Wang Y, You XF, Wang L, Ye WC, Li CC (2018) Chem Sci 9:1488

    CAS  PubMed  Google Scholar 

  303. Hou JQ, Guo C, Zhao JJ, He QW, Zhang BB, Wang HJ (2017) Org Chem 82:1448

    CAS  Google Scholar 

  304. Hiranrat W, Hiranrat A, Mahabusarakam W (2017) Phytochem Lett 21:25

    CAS  Google Scholar 

  305. Liu HX, Wang Y, Guo XY, Huo LQ, Xu ZF, Zhang WM, Qiu SX, Yang B, Tan HB (2018) Org Lett 20:546

    CAS  PubMed  Google Scholar 

  306. Zhang X, Wu G, Huo L, Guo X, Qiu S, Liu H, Tan H, Hu Y (2020) J Nat Prod 83:3

    CAS  PubMed  Google Scholar 

  307. Ippoliti FM, Barber JS, Tang Y, Garg NK (2018) J Org Chem 83:11323

    CAS  PubMed  PubMed Central  Google Scholar 

  308. Cai Y, Zhu H, Alperstein Z, Yu W, Cherkasov A, Zou H (2017) ACS Chem Biol 12:3086

    CAS  PubMed  Google Scholar 

  309. Tai H-M, Huang M-H, Yang C-C (2003) J Chin Chem Soc 50:441

    CAS  Google Scholar 

  310. Brown RT, Charalambides AA (1973) J Chem Soc Chem Commun 765

  311. Rakumitsu K, Sakamoto J, Ishikawa H (2019) Chem Eur J 25:8996

    CAS  PubMed  Google Scholar 

  312. Zhang S, Zhang Z-Y (2007) Drug Discov Today 12:373

    CAS  PubMed  Google Scholar 

  313. Li J, Guo Y, Zhou Z, Liu H, Gao L (2014) Granatumine A extracted from Xylocarpus granatum Koenig and preparation and application of the same. Chem Abstr 161:192540

    Google Scholar 

  314. Schuppe AW, Huang D, Chen Y, Newhouse TR (2018) J Am Chem Soc 140:2062

    CAS  PubMed  PubMed Central  Google Scholar 

  315. Schuppe AW, Zhao Y, Liu Y, Newhouse TR (2019) J Am Chem Soc 141:9191

    PubMed  PubMed Central  Google Scholar 

  316. Wezeman T, Brase S, Masters KS (2015) Nat Prod Rep 32:6

    CAS  PubMed  Google Scholar 

  317. Stewart M, Capon RJ, White JM, Lacey E, Tennant S, Gill JH, Shaddock MP (2004) J Nat Prod 67:728

    CAS  PubMed  Google Scholar 

  318. Nicolaou KC, Li A (2008) Angew Chem Int Ed 47:6579

    CAS  Google Scholar 

  319. Chen J, Li Y, Xiao Z, He H, Gao S (2020) Org Lett 25:8996

    Google Scholar 

  320. Yuan WH, Liu M, Jiang N, Guo ZK, Ma J, Zhang J, Song YC, Tan RX (2010) Eur J Org Chem 2010:6348

    Google Scholar 

  321. Han WB, Dou H, Yuan WH, Gong W, Hou YY, Ng SW, Tan RX (2015) Planta Med 81:145

    CAS  PubMed  Google Scholar 

  322. Sun Z-H, Liang F-L, Wu W, Chen Y-C, Pan Q-L, Li H-H, Ye W, Liu H-X, Li S-N, Tan G-H, Zhang W-M (2015) Molecules 20:22900

    CAS  PubMed  PubMed Central  Google Scholar 

  323. Kobayashi T, Takizawa I, Shinobe A, Kawamoto Y, Abe H, Ito H (2019) Org Lett 21:3008

    CAS  PubMed  Google Scholar 

  324. Atkins GM, Burgess EM (1968) J Am Chem Soc 90:4744

    CAS  Google Scholar 

  325. Yan Z, Zhao C, Gong J, Yang Z (2020) Org Lett 22:1644

    CAS  PubMed  Google Scholar 

  326. Han J-C, Liu X, Zhao J, Li S, Li C-C (2017) Tetrahedron 73:3289

    CAS  Google Scholar 

  327. Li J-L, Fu Y, Zhang H-Y, Zhao W-M (2015) Tetrahedron Lett 56:6503

    CAS  Google Scholar 

  328. Abe H, Sato S, Oishi W, Tamura M, Kobayashi T, Ito H (2019) Tetrahedron Lett 60:2059

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Majid M. Heravi or Vahideh Zadsirjan.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Heravi, M.M., Janati, F. & Zadsirjan, V. Applications of Knoevenagel condensation reaction in the total synthesis of natural products. Monatsh Chem 151, 439–482 (2020). https://doi.org/10.1007/s00706-020-02586-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-020-02586-6

Keywords

Navigation