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.
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Knoevenagel E (1922) Angew Chem 35:29
Jones G (1967) Org React 15:204
Knoevenagel E (1898) Ber Dtsch Chem Ges 31:2596
Knoevenagel E (1894) Ber Dtsch Chem Ges 27:2346
Knoevenagel E (1898) Ber Dtsch Chem Ges 31:2585
Knoevenagel E, Schmidt E (1894) Ann Chem 281:25
Knoevenagel E, Ruschhaupt W (1898) Ber Dtsch Chem Ges 31:1029
Knoevenagel E (1896) Ber Dtsch Chem Ges 29:172
Knoevenagel E (1894) Ber Dtsch Chem Ges 27:2345
Freeman F (1980) Chem Rev 80:329
Tietze LF (1996) Chem Rev 96:115
Tietze LF, Rackelmann N (2004) Pure Appl Chem 76:1967
Kraus GA, Krolski ME (1986) J Org Chem 51:3347
Zahouily M, Salah M, Bahlaouane B, Rayadh A, Houmam A, Hamed EA, Sebti S (2004) Tetrahedron 60:1631
Liang F, Pu YJ, Kurata T, Kido J, Nishide H (2005) Polymer 46:3767
Lipinska TM (2006) Tetrahedron 62:5736
Nic M, Jirat J, Kosata B, Jenkins A (1997) IUPAC compendium of chemical terminology, 2nd edn. Blackwell Scientific Publications, Oxford
Manske RHF (1965) The alkaloids: chemistry and physiology, vol 8. Academic Press, New York, p 673
Robbers JE, Speedie MK, Tyler VE (1996) Alkaloids. In: Balado D (ed) Pharmacognosy and pharmacobiotechnology, 9th edn. Lippincott Williams & Wilkins, Philadelphia
Heravi MM, Hamidi H, Zadsirjan V (2014) Curr Org Synth 11:647
Heravi MM, Lashaki TB, Fattahi B, Zadsirjan V (2018) RSC Adv 8:6634
Koshvandi ATK, Heravi MM (2018) Appl Organomet Chem 32:3
Heravi MM, Rohani S, Zadsirjan V, Zahedi N (2017) RSC Adv 7:52852
Heravi MM, Asadi S, Nazari N (2016) Monatsh Chem 147:961
Heravi MM, Asadi S, Nazari N, Lashkariani BM (2016) Curr Org Synth 13:308
Heravi MM, Fard MV, Faghihi Z (2015) Curr Org Chem 19:1491
Heravi MM, Zadsirjan V, Farajpour B (2016) RSC Adv 6:30498
Heravi MM, Lashaki TB, Poorahmad N (2015) Tetrahedron Asymmetry 26:405
Heravi MM, Ahmadi T, Ghavidel M (2015) RSC Adv 5:101999
Heravi MM, Fard MV, Nazari N (2015) Curr Org Chem 19:2358
Heravi MM, Asadi S, Nazari N (2015) Curr Org Chem 19:2196
Heravi MM, Vavsari VF (2015) RSC Adv 5:50890
Heravi MM, Hashemi E, Nazari N (2014) Mol Divers 18:441
Heravi MM, Hashemi E, Azimian F (2014) Tetrahedron 70:7
Heravi MM, Zadsirjan V, Bozorgpour Savadjani Z (2014) Curr Org Chem 18:2857
Heravi MM, Bakhtiari A, Faghihi Z (2014) Curr Org Synth 11:787
Heravi MM, Zadsirjan V (2013) Tetrahedron Asymmetry 24:1149
Heravi MM, Hashemi E, Ghobadi N (2013) Curr Org Chem 17:2192
Heravi MM, Hashemi E (2012) Tetrahedron 68:9145
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
Marin I, Abad JP, Urena D, Amils R (1995) Biochemistry 34:16519
Tan GT, Pezzuto JM, Kinghorn AD, Hughes SH (1991) J Nat Prod 54:143
Kametani T, Suzuki Y, Ihara M (1979) Can J Chem 57:1679
Openshaw HT, Robson NC, Whittaker N (1969) J Chem Soc 101
Brauchli P, Deulofeu V, Budzikiewicz H, Djerassi C (1964) J Am Chem Soc 86:1895
Naito T, Kojima N, Ninomiya I (1986) Chem Pharm Bull 34:3530
Fujii T, Yoshifuji S (1979) Chem Pharm Bull 27:1486
Kametani T, Surgenor SA, Fukumoto K (1981) J Chem Soc 920
Ito A, Lee YH, Chai HB, Gupta MP, Farnsforth NR, Gordell GA, Pezzuto JM, Kinghorn AD (1999) J Nat Prod 62:1346
Tietze LF, Bachmann J, Wichmann J, Zhou Y, Raschke T (1997) Liebigs Ann/Recl 1997:881
Tietze LF, Bachmann J, Wichmann J, Burkhardt O (1994) Synthesis 1994:1185
Tietze LF, Zhou Y (1999) Angew Chem Int Ed 38:2045
Tietze LF, Rackelmann N, Sekar G (2003) Angew Chem Int Ed 42:4254
Tietze LF, Rackelmann N, Muller I (2004) Chem Eur J 10:2722
Farmer RL, Biddle MM, Nibbs AE, Huang XK, Bergan RC, Scheidt KA (2010) ACS Med Chem Lett 1:400
Biddle MM, Lin M, Scheidt KA (2007) J Am Chem Soc 129:3830
Custar DW, Zabawa TP, Scheidt KA (2008) J Am Chem Soc 130:804
Snider BB, Kwon T (1992) J Org Chem 57:2399
Rebecca L, Farmer A, Scheidt K (2013) Chem Sci 4:3304
Morita H, Hirasawa Y, Shinzato T, Kobayashi J (2004) Tetrahedron 60:7015
Morita H, Hirasawa Y, Yoshida N, Kobayashi J (2001) Tetrahedron Lett 42:4199
Hirasawa Y, Morita H, Kobayashi J (2003) Tetrahedron 59:3567
Hirasawa Y, Morita H, Kobayashi J (2004) Heterocycles 64:515
Ma X, Gang DR (2004) Nat Prod Rep 21:752
Snider BB, Grabowski JF (2007) J Org Chem 72:1039
Michael JP (2007) Nat Prod Rep 24:191
Ohmiya S, Saito K, Murakoshi I (1995) Lupine alkaloids. In: Cordell GA (ed) The alkaloids: chemistry and pharmacology, 47th edn. Academic Press, New York
Leonard NJ (1953) Lupin alkaloids. In: Manske RHF, Holmes HL (eds) The alkaloids: chemistry and physiology, 3rd edn. Academic Press, New York
Leonard NJ (1960) Lupin alkaloids. In: Manske RHF (ed) The alkaloids: chemistry and physiology, 7th edn. Academic Press, New York
Norcross NR, Melbardis JP, Solera MF, Sephton MA, Kilner C, Zakharov LN, Astles PC, Warriner SL, Blakemore PR (2008) J Org Chem 73:7939
Aoki S, Watanabe Y, Sanagawa M, Setiawan A, Kotoku N, Kobayashi M (2006) J Am Chem Soc 128:3148
Watanabe Y, Aoki S, Tanabe D, Setiawan A, Kobayashi M (2007) Tetrahedron 63:4074
Yamashita S, Iso K, Kitajima K, Himuro M, Hirama M (2011) J Org Chem 76:2408
Liu ZJ, Lu R (1988) Gelsemium alkaloids. In: Brossi A (ed) The alkaloids: chemistry and pharmacology, 33rd edn. Academic Press, New York
Saxton JE (1965) Alkaloids of gelsemium species. In: Manske RHF (ed) The alkaloids: chemistry and physiology, 8th edn. Academic Press, New York
Lovell L, Pepinsky R, Wilson AJC (1959) Tetrahedron Lett 4:1
Conroy H, Chakrabarti JK (1959) Tetrahedron Lett 4:6
Kondo K, Umemoto T, Yako K, Tunemoto D (1978) Tetrahedron Lett 19:3927
Fukuyama T, Liu G (1996) J Am Chem Soc 118:7426
Nakano H, Matsuda Y, Ito K, Ohkubo S, Morimoto M, Tomita F (1981) J Antibiot 34:266
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
Takahashi K, Yoshida M, Tomita F, Shirahata K (1981) J Antibiot 34:271
Hirayama N, Takahashi K, Shirahata K, Ohashi Y, Sasada Y (1981) Bull Chem Soc Jpn 54:1338
Mishra R, Tritch HR, Pandey RC (1985) J Antibiot 38:1280
Tse-Dinh TC, McGee LR (1987) Biochem Biophys Res Commun 143:808
Tomito F, Takahashi KI, Tamaoki T (1982) J Antibiot 35:1038
Elespuru RK, Gonda SK (1984) Science 223:69
McGee LR, Mishra R (1990) J Am Chem Soc 112:2386
Morimoto M, Okubo S, Tomito F, Marumo H (1981) J Antibiot 34:701
Matsumoto A, Fujiwara Y, Elespuru RK, Hanawalt PC (1994) Photochem Photobiol 60:225
Reddy P, Nandaluru J, Bodwell J (2012) Org Chem 77:8028
TePaske MR, Gloer JB, Wicklow DT, Dowd PF (1991) Tetrahedron Lett 32:5687
Tietze LF, Geissler H, Fennen J, Brumby T, Brand S, Schulz G (1994) J Org Chem 59:182
Teitze LF, Beifuss U (1993) Angew Chem Int Ed 32:131
Tietze LF (1990) J Heterocycl Chem 27:47
Matlin SA, Sammes PG, Upton RM (1979) J Chem Soc 2481
Rigby JH, Qabar M (1989) J Org Chem 54:5852
Snider BB, Lu Q (1996) J Org Chem 61:2839
Kakeya H, Kageyama S, Nie L, Onose R, Okada G, Beppu T, Norbury CJ, Osada H (2001) J Antibiot 54:850
Kakeya H, Takahashi I, Okada G, Isono K, Osada H (1995) J Antibiot 48:733
Hayashi Y, Kanayama J, Yamaguchi J, Shoji M (2002) J Org Chem 67:9443
Brady SF, Singh MP, Janso JE, Clardy J (2000) J Am Chem Soc 122:2116
Singh MP, Janso JE, Luckman SW, Brady SF, Clardy J, Greenstein M, Maiese WM (2000) J Antibiot 53:256
Brady SF, Bondi SM, Clardy J (2001) J Am Chem Soc 123:9900
Mandal M, Yun H, Dudley GB, Lin S, Tan DS, Danishefsky SJ (2005) J Org Chem 70:10619
Gan C-Y, Low Y-Y, Etoh T, Hayashi M, Komiyama K, Kam T-S (2009) J Nat Prod 72:2098
Basha A, Lipton M, Weinreb SM (1977) Tetrahedron Lett 18:4171
Sirasani G, Andrade RB (2011) Org Lett 13:17
Johnson G, Sunderwirth SG, Gibian H, Coulter AW, Gassner FX (1963) Phytochemistry 2:145
Kelley CJ, Harruff RC, Carmack M (1976) J Org Chem 41:449
Kelley CJ, Mahajan JR, Brooks LC, Neubert LA, Breneman WR, Carmack M (1975) J Org Chem 40:1804
Wagner H, Whittmann D, Schafer W (1975) Tetrahedron Lett 16:547
Chen L, Wang W-Y, Wang Y-P (2009) Acta Pharm Sin 30:1245
Ghosh AK, Cheng X, Zhou B (2012) Org Lett 14:19
Gürtler H, Pedersen R, Anthoni U, Christophersen C, Nielsen PH, Wellington EMH, Pedersen C, Bock K (1994) J Antibiot 47:434
Kobayashi T, Kon Y, Abe H, Ito H (2014) Org Lett 16:6397
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
Reckendorf WM (1966) Angew Chem Int Ed 5:665
Shibuya M, Jaisli F, Eschenmoser A (1979) Angew Chem Int Ed 18:636
Bohlmann F, Jakupovic J, Misra LN, Castro V (1985) Liebigs Ann Chem 1985:1367
Herath HMTB, Priyadarshani AMA, Jamie J (1998) Nat Prod Lett 12:91
Ferris GE, Hong K, Roundtree IA, Morken JP (2013) J Am Chem Soc 135:2501
Wanner MJ, Boots RNA, Eradus B, Gelder RD, van Maarseveen JH, Hiemstra H (2009) Org Lett 11:2579
Reyes E, Talavera G, Vicario JL, Badía D, Carrillo L (2009) Angew Chem Int Ed 48:5701
Michrowska A, List B (2009) Nat Chem 1:225
Jones SB, Simmons B, Mastracchio A, MacMillan DWC (2011) Nature 475:183
Tan H, Chen X, Chen H, Liu H, Qiu S (2015) Eur J Org Chem 2015:4956
Herath HMTB, Padmasiri W (1999) Nat Prod Lett 14:141
Herath HMTB, Priyadarshani AMA, Jamie J (1996) Phytochemistry 42:1439
Herath HMTB, Priyadarshani AMA, Jamie J (1997) Phytochemistry 44:699
Tan H, Liu H, Chen X, Chen H, Qiu S (2015) Org Biomol Chem 13:9977
Wang W, Kim H, Nam S-J, Rho BJ, Kang H (2012) J Nat Prod 75:2049
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
Liang J, Hu W, Tao P, Jia Y (2013) J Org Chem 78:5810
Roy S, Davydova MP, Pal R, Gilmore K, Tolstikov GA, Vasilevsky SF, Alabugin IV (2011) J Org Chem 76:7482
Boukouvalas J, Thibault C (2015) J Org Chem 80:681
Quinoa K, Crews PP (1987) Tetrahedron Lett 28:3229
Rodriguez AD, Akee RK, Scheuer PJ (1987) Tetrahedron Lett 28:4989
Arabshahi L, Schmitz FJ (1987) J Org Chem 52:3584
Kim D, Lee IS, Jung JH, Yang S-I (1999) Arch Pharm Res 22:25
Kim D, Lee IS, Jung JH, Lee CO, Choi SU (1999) Anticancer Res 19:4085
Jung JH, Sim CJ, Lee CO (1995) J Nat Prod 58:1722
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
Shin J, Lee H-S, Seo Y, Rho JR, Cho KW, Paul VJ (2000) Tetrahedron 56:9071
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
Hong S, Lee M, Jung M, Park Y, Kim M-H, Park H-G (2012) Tetrahedron Lett 53:4209
Miao S, Andersen RJ (1991) J Org Chem 56:6275
Ortega MJ, Zubia E, Ocana JM, Naranjo S, Salva J (2000) Tetrahedron 56:3963
Kotora M, Negishi E (1997) Synthesis 1997:121
Boukouvalas J, Lachance N, Ouellet M, Trudeau M (1998) Tetrahedron Lett 39:7665
Prim D, Fuss A, Krisch G, Silva AMS (1999) J Chem Soc Perkin Trans 1175
Chavan SP, Pathak AB, Pandey A, Kalkote UR (2007) Synth Commun 37:4253
Chen YS, Lee SM, Lin YJ, Chiang SH, Lin ChCh (2014) Molecules 19:2029
Wang BQ (2010) J Med Plants Res 4:2813
Lam FFY, Yeung JHK, Chan KM, Or PMY (2007) Vasc Pharmacol 46:271
Shen Y, Hu Y, Zhang Y (2011) Hypertens Pregnancy 30:465
Sidoryk K, Filip K, Cmoch P, Laszcz M, Cybulski M (2018) J Mol Struct 1153:135
Li XL, Xu MJ, Zhao YL, Xu J (2010) Molecules 15:9298
Campaigne E, Hutchinson JH (1970) J Heterocycl Chem 7:655
Lawson W, Perkin WH, Robinson R (1924) J Chem Soc 125:626
Godard A, Queguiner G (1980) J Heterocycl Chem 17:465
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
ElSohly MA, Slade D (2005) Life Sci 78:539
Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, Bonner TI (1990) Nature 365:61
Munro S, Thomas KL, Abu-Shaar M (1993) Nature 365:61
Marriot KS, Huffman JW (2008) Curr Top Med Chem 8:187
Pertwee RG (1997) Pharmacol Ther 74:129
Nandaluru PR, Bodwell GJ (2012) Org Lett 14:1
Baeckstrom P, Sundstrom G (1970) Acta Chem Scand 24:716
Torang J, Nieger M, Brase S (2005) Synthesis 2005:1888
Saleem M, Hussain H, Ahmed I, van Reec T, Krohn K (2011) Nat Prod Rep 28:1534
Chen DYK (2011) Synlett 2011:2459
Tiefenbacher K, Mulzer J (2008) Angew Chem Int Ed 47:2548
Wang Z (2012) Synlett 23:2311
Gao P, Hou TP, Gao R, Cui Q, Liu SG (2001) Pest Manag Sci 57:307
Kogiso SM, Hosozawa S, Wada K, Munakata K (1974) Phytochemistry 13:2332
Xu G, Yang X, Jiang B, Lei P, Liu X, Wang Q, Zhang X, Ling Y (2016) Bioorg Med Chem Lett 26:1849
Ward RS (1999) Nat Prod Rep 16:75
Lee S, Yoo HH, Piao XL, Kim JS, Kang SS, Shin KH (2005) Arch Pharm Res 28:186
Janmanchi D, Lin CH, Hsieh J-Y, Tseng Y-P, Chen T-A, Jhuang H-J, Yeh SF (2013) Bioorg Med Chem 21:2163
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
Kao T-T, Lin C-C, Shia K-S (2015) J Org Chem 80:6708
Clifford MN, Marks S, Knight S, Kuhnert N (2006) J Agric Food Chem 54:4095
Robinson WE Jr, Reinecke MG, Abdel-Malek S, Chow SA (1996) Proc Natl Acad Sci USA 93:6326
Tamura H, Akioka T, Ueno K, Chujyo T, Okazaki K-I, King PJ, Robinsion WE (2006) Mol Nutr Food Res 50:396
Ojwang JO, Wang Y-H, Wyde PR, Fischer NH, Schuehly W, Appleman JR, Hinds S, Shimasaki CD (2005) Antiviral Res 68:163
Antonio AG, Moraes RS, Perrone D, Maia LC, Santos KN, Lurio NLP, Farah A (2010) Food Chem 118:782
Raheem KS, Botting NP, Williamson G, Barron D (2011) Tetrahedron Lett 52:7175
Dao TT, Tran TL, Kim J, Nguyen PH, Lee EH, Park J, Jang IS, Oh WK (2012) J Nat Prod 75:1332
Bigi F, Carloni S, Ferrari L, Maggi R, Mazzacani A, Sartori G (2001) Tetrahedron Lett 42:5203
Silva AC, Benelkebir H, Lopes RSC, Lopesa CC, Ganesan A (2018) J Braz Chem Soc 29:1157
Sun Y, Tian L, Huang J, Ma H-Y, Zheng Z, Lv A-L, Yasukawa K, Pei Y-H (2008) Org Lett 10:393
Myers E, Herrero-Gómez E, Baitinger I, Lachs J, Mayer P, Hanni M, Ochsenfeld C, Trauner D (2014) J Org Chem 79:9812
Harrity JPA, Provoost O (2005) Org Biomol Chem 3:1349
Hsung RP, Kurdyumov AV, Sydorenko N (2005) Eur J Org Chem 2005:23
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
Xu X, Doyle MP (2014) Acc Chem Res 47:1396
Moyano A, Rios R (2011) Chem Rev 111:4703
Fotiadou D, Zografos AL (2012) Org Lett 14:5664
Hu J, Dong W, Wu X-Y, Tong X (2012) Org Lett 14:5530
Bulger PG, Bagal SK, Marquez R (2008) Nat Prod Rep 25:254
Luoa G-Y, Wua H, Tang Y, Lia H, Yeomb H-S, Yanga K, Hsung RP (2015) Synthesis 47:2713
Murrayamine M, Wu T-S, Wang M-L, Wu P-L, Ito C, Furukawa H (1996) Phytochemistry 41:1433
Duffield AM, Jefferies PR, Maslen FN, Roe AM (1963) Tetrahedron 19:593
Crombie L, Redshaw SD, Black DA, Whiting DA (1979) J Chem Soc Chem Commun 628
Crombie L, Redshaw SD, Black DA, Whiting DA (1983) J Chem Soc Perkin Trans 1:1411
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
Cheng S-Y, Huang K-J, Wang S-K, Wen Z-H, Chen P-W, Duh C-Y (2010) J Nat Prod 73:771
Lam HC, Pepper HP, Sumby CJ, George JH (2017) Angew Chem Int Ed 56:1
Xu J, Lacoske MH, Theodorakis EA (2014) Angew Chem Int Ed 53:956
Akagi M, Matsui N, Akae H, Hirashima N, Fukuishi N, Fukuyama Y, Akagi R (2015) J Pharmacol Sci 127:155
Carcache DA, Cho YS, Hua Z, Tian Y, Li Y-M, Danishefsky SJ (2006) J Am Chem Soc 128:1016
Trzoss L, Xu J, Lacoske MH, Mobley WC, Theodorakis EA (2013) Chem Eur J 19:6398
Wolinsky J, Chan D (1965) J Org Chem 30:41
Marx JN, Norman LR (1975) J Org Chem 40:1602
Gomes J, Daeppen C, Liffert R, Roesslein J, Kaufmann E, Heikinheimo A, Neuburger M, Gademann K (2016) J Org Chem 81:11017
Bauer I, Knölker H-J (2012) Top Curr Chem 309:203
Schmidt AW, Reddy KR, Knölker H-J (2012) Chem Rev 112:3193
Hesse R, Gruner KK, Kataeva O, Schmidt AW, Knölker H-J (2013) Chem Eur J 19:14098
Dai J, Ma D, Fu C, Ma S (2015) Eur J Org Chem 2015:5655
Singh IP, Bharate SB (2006) Nat Prod Rep 23:558
Chen J, Craven LA (2007) Flora of China, vol 13. Science Press/Missouri Botanical Garden Press, Beijing, p 330
Lavanya G, Voravuthikunchai SP, Towatana NH (2012) J Evid Based Complement Altern Med 2012:535479
Liu H-X, Zhang WM, Xu Z-F, Chen Y-C, Tan H-B, Qiu S-X (2016) RSC Adv 6:25882
Liu H-X, Chen K, Tang G-H, Yuan Y-F, Tan H-B, Qiu S-X (2016) RSC Adv 6:25882
Chen T, Yu CG, Yang BL (2011) Chem Nat Compd 47:524
Joab D, Han S (2017) Org Chem Front 4:506
Zou Y, Xu W, Tsunematsu Y, Tang M, Watanabe K, Tang Y (2014) Org Lett 16:6390
Stierle AA, Stierle DB, Patacini B (2008) J Nat Prod 71:856
Wiemann P, Guo CJ, Palmer JM, Sekonyela R, Wang CCC, Keller NP (2013) Proc Natl Acad Sci USA 110:17065
Tsunematsu Y, Fukutomi M, Saruwatari T, Noguchi H, Hotta K, Tang Y, Watanabe K (2014) Angew Chem Int Ed 53:8475
Asami Y, Kakeya H, Onose R, Yoshida A, Matsuzaki H, Osada H (2002) Org Lett 4:2845
Asami Y, Kakeya H, Komi Y, Kojima S, Nishikawa K, Beebe K, Neckers L, Osada H (2008) Cancer Sci 99:1853
Carbone M, Nunez-Pons L, Castellucccio F, Avila C, Gavagnin M (2009) J Nat Prod 72:1357
Palermo JA, Rodriguez Brasco MF, Spagnuolo C, Seldes AM (2000) J Org Chem 65:4482
Castillo UF, Sakagami Y, Alonso-Amelot M, Ojika M (1999) Tetrahedron 55:12295
Finkielsztein LM, Bruno AM, Renou SG, Iglesias GY (2006) Bioorg Med Chem 14:1863
Pettit GR, Meng Y, Pettit RK, Herald DL, Cichacz ZA, Doubek DL, Richert L (2010) J Nat Prod 73:388
Suresh M, Kumar N, Veeraraghavaiah G, Hazra S, Singh RB (2016) J Nat Prod 79:2740
Roethle PA, Trauner D (2008) Nat Prod Rep 25:298
Li Y, Pattenden G (2011) Nat Prod Rep 28:1269
Missakian MG, Burresons BJ, Scheuer PJ (1975) Tetrahedron 31:2513
Fenical W, Okuda RK, Banduragga MM, Culver P, Jacobs RS (1981) Science 212:1512
Tang B, Bray CD, Pattenden G (2009) Org Biomol Chem 7:4448
Tang B, Bray CD, Pattenden G, Rogers J (2010) Tetrahedron 66:2492
McAulay K, Clark JS (2017) Chem Eur J 23:9761
Hu L-Z, Zhang Y, Zhu H-C (2016) Org Lett 18:2272
Li C-J, Ma J, Sun H, Zhang D, Zhang D-M (2016) Org Lett 18:168
Cottiglia F, Casu L, Leont M (2012) J Nat Prod 75:225
Zhou W-L, Tan H-B, Qiu S-X, Chen G-Y, Liu H-X, Zheng C (2017) Tetrahedron Lett 58:1817
Schroeder FC, Kau TR, Silver PA, Clardy J (2005) J Nat Prod 68:574
Gribble GW (2012) Occurrence of halogenated alkaloids. In: Knölker HJ (ed) The alkaloids: chemistry and biology, 71st edn. Academic Press, New York
Boccitto M, Lee N, Sakamoto S, Spruce LA, Handa H, Clardy J, Seeholzer SH, Kalb RG (2017) Mar Drugs 15:246
Xu J, Wanga K, Wu J (2018) RSC Adv 8:13747
Welch WM, Kraska AR, Sarges R, Koe BK (1984) J Med Chem 27:1508
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
Bogeso KP, Christensen AV, Hyttel J, Liljefors T (1985) J Med Chem 28:1817
Lee BH, Choi YL, Shin S, Heo JN (2011) J Org Chem 76:6611
Ryabukhin SV, Plaskon AS, Volochnyuk DM, Pipko SE, Shivanyuk AN, Tolmachev AA (2007) J Comb Chem 9:1073
Drago C, Caggiano L, Jackson RF (2005) Angew Chem Int Ed 44:7221
Tang M-L, Peng P, Liu Z-Y, Zhang J, Yu J-M, Sun X (2016) Chem Eur J 22:14535
Kobayashi J, Kubota T (2009) Nat Prod Rep 26:936
Chattopadhyay AK, Hanessian S (2017) Chem Rev 117:4104
Zhang H, Zhang D-D, Li J-Y, Shyaula SL, Li J, Yue J-M (2016) RSC Adv 6:44402
Lopez AM, Ibrahim AA, Rosenhauer GJ, Sirinimal HS, Stockdil L (2018) Org Lett 20:2216
Dalessandro EV, Collin HP, Guimarães LGL, Valle MS, Pliego JR (2017) J Phys Chem B 121:5300
Hamlin AM, Kisunzu JK, Sarpong R (2014) Org Biomol Chem 12:1846
Liu X-Y, Qin Y (2015) Asian J Org Chem 4:1010
Zhu G, Liu R, Liu B (2015) Synthesis (Mass) 47:2691
Chen K, Baran PS (2009) Nature 459:824
Wang F-P, Chen Q-H, Liu X-Y (2010) Nat Prod Rep 27:529
Gong CH, Liu X-Y, Wang Z-X, Nie W, Qin Y (2016) Nat Commun 7:12183
Maslovskaya LA, Savchenko AI, Krenske EH, Gordon VA, Reddell PW, Pierce CJ, Parsons PG, Williams CM (2014) Chem Comm 50:12315
Zhang XL, Wang L, Li F, Yu K, Wang MK (2013) J Nat Prod 76:858
Hanson JR (2012) Nat Prod Rep 29:890
Hanson JR (2013) Nat Prod Rep 30:1346
Thombal RS, Jadhav VH (2015) Org Biomol Chem 13:9485
Nair MSR, Takeshita H, McMorris TC, Anchel M (1969) J Org Chem 34:240
Woodward RB, Hoye TR (1977) J Am Chem Soc 99:8007
Morrison AE, Hoang TT, Birepinte M, Dudley GB (2017) Org Lett 19:858
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
Wiest JM, Bach T (2016) J Org Chem 81:6149
Rutkowski J, Brzezinski B (2013) Biomed Res Int 2013:162513
Wang B-G, Gloer JB, Ji N-Y, Zhao J-C (2013) Chem Rev 113:3632
Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR (2013) Nat Prod Rep 30:237
Kurosawa E, Fukuzawa A, Irie T (1972) Tetrahedron Lett 21:2121
Suzuki T, Koizumi K, Suzuki M, Kurosawa E (1983) Chem Lett 12:1643
Martín T, Padrón JI, Martín VS (2014) Synlett 25:12
Li E, Jiang L, Guo L, Zhang H, Che Y (2008) Bioorg Med Chem 16:7894
Zask A, Ellestad G (2018) Chirality 30:157
Wei M-Y, Li D, Shao C-L, Deng D-S, Wang C-Y (2013) Mar Drugs 11:1050
Arredondo V, Roa DE, Yan S, Liu-Smith F, Van Vranken DL (2019) Org Lett 21:1755
Wang FP, Chen QH (2010) The C19-diterpenoid alkaloids. In: Cordell GA (ed) The alkaloids: chemistry and biology, 69th edn. Elsevier Science, New York
Tashkhodzhaev B, Saidkhodzhaeva SA, Bessonova IA, Antipin MY (2000) Chem Nat Compd 36:79
Nie W, Gong J, Chen Z, Liu J, Tian D, Song H, Liu X-Y, Qin Y (2019) J Am Chem Soc 141:9712
O’Connor SE, Maresh JJ (2006) Nat Prod Rep 23:532
Szabó LF (2008) Molecules 13:1875
Lémus C, Kritsanida M, Canet A, Genta-Jouve G, Michel S, Deguin B, Grougnet R (2015) Tetrahedron Lett 56:5377
Li L, Yuan K, Jia Q, Jia Y (2019) Angew Chem Int Ed 58:6074
Douki K, Shimokawa J, Kitamura M (2019) Org Biomol Chem 17:1727
Dou Y, Kouklovsky C, Gandon V, Vincent G (2019) Angew Chem Int Ed 59:1527
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
Hou JQ, Guo C, Zhao JJ, He QW, Zhang BB, Wang HJ (2017) Org Chem 82:1448
Hiranrat W, Hiranrat A, Mahabusarakam W (2017) Phytochem Lett 21:25
Liu HX, Wang Y, Guo XY, Huo LQ, Xu ZF, Zhang WM, Qiu SX, Yang B, Tan HB (2018) Org Lett 20:546
Zhang X, Wu G, Huo L, Guo X, Qiu S, Liu H, Tan H, Hu Y (2020) J Nat Prod 83:3
Ippoliti FM, Barber JS, Tang Y, Garg NK (2018) J Org Chem 83:11323
Cai Y, Zhu H, Alperstein Z, Yu W, Cherkasov A, Zou H (2017) ACS Chem Biol 12:3086
Tai H-M, Huang M-H, Yang C-C (2003) J Chin Chem Soc 50:441
Brown RT, Charalambides AA (1973) J Chem Soc Chem Commun 765
Rakumitsu K, Sakamoto J, Ishikawa H (2019) Chem Eur J 25:8996
Zhang S, Zhang Z-Y (2007) Drug Discov Today 12:373
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
Schuppe AW, Huang D, Chen Y, Newhouse TR (2018) J Am Chem Soc 140:2062
Schuppe AW, Zhao Y, Liu Y, Newhouse TR (2019) J Am Chem Soc 141:9191
Wezeman T, Brase S, Masters KS (2015) Nat Prod Rep 32:6
Stewart M, Capon RJ, White JM, Lacey E, Tennant S, Gill JH, Shaddock MP (2004) J Nat Prod 67:728
Nicolaou KC, Li A (2008) Angew Chem Int Ed 47:6579
Chen J, Li Y, Xiao Z, He H, Gao S (2020) Org Lett 25:8996
Yuan WH, Liu M, Jiang N, Guo ZK, Ma J, Zhang J, Song YC, Tan RX (2010) Eur J Org Chem 2010:6348
Han WB, Dou H, Yuan WH, Gong W, Hou YY, Ng SW, Tan RX (2015) Planta Med 81:145
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
Kobayashi T, Takizawa I, Shinobe A, Kawamoto Y, Abe H, Ito H (2019) Org Lett 21:3008
Atkins GM, Burgess EM (1968) J Am Chem Soc 90:4744
Yan Z, Zhao C, Gong J, Yang Z (2020) Org Lett 22:1644
Han J-C, Liu X, Zhao J, Li S, Li C-C (2017) Tetrahedron 73:3289
Li J-L, Fu Y, Zhang H-Y, Zhao W-M (2015) Tetrahedron Lett 56:6503
Abe H, Sato S, Oishi W, Tamura M, Kobayashi T, Ito H (2019) Tetrahedron Lett 60:2059
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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
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DOI: https://doi.org/10.1007/s00706-020-02586-6