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Monosaccharides as Chiral Pools for the Synthesis of Complex Natural Compounds

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Book cover Glycoscience

Abstract

A variety of complex natural compounds are synthesized by using monosaccharides as chiral starting materials. Exemplifying eight representative natural products, i. e., erythromycins, elaiophilin, herbimaycins, calbistrin A, lactacystin, tautomycin, FK-506, and halichondrin B, the methodology how monosaccharides are incorporated into natural product synthesis as chiral pools is described.

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Abbreviations

AIBN:

2,2′-azobisisobutyronitrile

All:

allyl

CSA:

10-camphorsulfonic acid

DDQ:

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DEAD:

diethyl azodicarboxylate

DEIPS:

diethylisopropylsilyl

DHQD:

dihydroquinidine p-chlorobenzoate

DIAD:

diisopropyl azodicarboxylate

DIBALH:

diisobutylaluminum hydride

DMAP:

4-(dimethylamino)pyridine

DME:

1,2-dimethoxyethane

DMF:

N, N-dimethylformamide

DMSO:

dimethyl sulfoxide

HMPA:

hexamethylphosphoramide

LDA:

lithium diisopropylamide

LHMDS:

lithium bis(trimethylsilyl)amide

m-CPBA:

3-chloroperoxybenzoic acid

MMTr:

1-(bis(4-methoxyphenyl))-1-phenylmethyl

MOM:

methoxymethyl

MP:

4-methoxyphenyl

MPM:

(4-methoxyphenyl)methyl

Ms:

methanesulfonyl

NBS:

N-bromosuccinimide

NIS:

N-iodosuccinimide

NMO:

4-methylmorpholine N-oxide

PCC:

pyridinium chlorochromate

PDC:

pyridinium dichromate

PPTS:

pyridinium p-toluenesulfonate

TBAF:

tetrabutylammonium fluoride

TBDMS:

t-butyldimethylsilyl

TBDMSOTf:

t-butyldimethylsilyl trifluoromethanesulfonate

TBDPSCl:

t-butyldiphenylsilyl chloride

TFA:

trifluoroacetic acid

THF:

tetrahydrofuran

THP:

tetrahydropyranyl

Tf:

trifluoromethanesulfonyl

Tr:

triphenylmethyl

Ts:

p-toluenesulfonyl

TMEDA:

N, N, N′, N′-tetramethylethylenediamine

TMSCl:

trimethylsilyl chloride

References

  1. Vasella A (1980) Chiral building blocks in enantiomer synthesis. In: Scheffold R (ed) Modern Synthetic Methods. Otto Salle Verlag GmbH & Co., Frankfurt am Main, p 173

    Google Scholar 

  2. Hanessian S (1983) Total Synthesis of Natural Products: the `Chiron' Approach. Pergamon Press, Oxford

    Google Scholar 

  3. Lichtenthaler FW (1992) Enantiopure building blocks from sugars and their utilization in natural product synthesis. In: Scheffold R (ed) Modern Synthetic Methods. VHCA, Basel, p 273

    Google Scholar 

  4. Collins PM, Ferrier RJ (1995) Monosaccharides. Wiley, Chichester

    Google Scholar 

  5. Bols M (1996) Carbohydrate Building Blocks. Wiley, New York

    Google Scholar 

  6. Tatsuta K (1997) J Syn Org Chem Jpn 55:970

    CAS  Google Scholar 

  7. Hanessian S (ed) (1997) Preparative Carbohydrate Chemistry. Marcel Dekker, New York

    Google Scholar 

  8. Woodward RB et al. (1981) J Am Chem Soc 103:3210

    Article  CAS  Google Scholar 

  9. Woodward RB et al. (1981) J Am Chem Soc 103:3213

    Article  CAS  Google Scholar 

  10. Woodward RB et al. (1981) J Am Chem Soc 103:3215

    Article  CAS  Google Scholar 

  11. Corey EJ, Trybulski EJ, Melvin LS Jr., Nicolaou KC, Secrist JA, Lett R, Sheldrake PW, Falck JR, Brunelle DJ, Haslanger MF, Kim S, Yoo S (1978) J Am Chem Soc 100:4618

    Article  CAS  Google Scholar 

  12. Corey EJ, Kim S, Yoo S, Nicolaou KC, Melvin LS Jr., Brunelle DJ, Falck JR, Trybulski EJ, Lett R, Scheldrake PW (1978) J Am Chem Soc 100:4620

    Article  CAS  Google Scholar 

  13. Corey EJ, Hopkins PB, Kim S, Yoo S, Nambiar KP, Falck JR (1979) J Am Chem Soc 101:7131

    Article  CAS  Google Scholar 

  14. Kinoshita M, Ohsawa N, Gomi S (1982) Carbohydr Res 109:5

    Article  CAS  Google Scholar 

  15. Kinoshita M, Arai M, Tomooka K, Nakata M (1986) Tetrahedron Lett 27:1811

    Article  CAS  Google Scholar 

  16. Kinoshita M, Arai M, Ohsawa N, Nakata M (1986) Tetrahedron Lett 27:1815

    Article  CAS  Google Scholar 

  17. Nakata M, Arai M, Tomooka K, Ohsawa N, Kinoshita M (1989) Bull Chem Soc Jpn 62:2618

    Article  CAS  Google Scholar 

  18. Toshima K, Mukaiyama S, Yoshida T, Tamai T, Tatsuta K (1991) Tetrahedron Lett 32:6155

    Article  CAS  Google Scholar 

  19. Toshima K, Nozaki Y, Mukaiyama S, Tamai T, Nakata M, Tatsuta K, Kinoshita M (1995) J Am Chem Soc 117:3717

    Article  CAS  Google Scholar 

  20. Sviridov AF, Ermolenko MS, Yashunsky DV, Borodkin VS, Kochetkov NK (1987) Tetrahedron Lett 28:3835

    Article  CAS  Google Scholar 

  21. Kochetkov NK, Sviridov AF, Ermolemko MS, Yashunsky DV, Borodkin VS (1989) Tetrahedron 45:5109

    Article  CAS  Google Scholar 

  22. Nakata M, Akiyama N, Kamata J, Kojima K, Masuda H, Kinoshita M, Tatsuta K (1990) Tetrahedron 46:4629

    Article  CAS  Google Scholar 

  23. Kochetkov NK, Sviridov AF, Ermolenko MS (1981) Tetrahedron Lett 22:4315

    Article  CAS  Google Scholar 

  24. Kochetkov NK, Sviridov AF, Ermolenko MS (1981) Tetrahedron Lett 22:4319

    Article  CAS  Google Scholar 

  25. Kochetkov NK, Sviridov AF, Ermolenko MS, Yashunsky DV (1984) Tetrahedron Lett 25:1605

    Article  CAS  Google Scholar 

  26. Sviridov AF, Ermolenko MS, Yashunsky DV, Borodkin VS, Kochetkov NK (1987) Tetrahedron Lett 28:3839

    Article  CAS  Google Scholar 

  27. Sviridov AF, Borodkin VS, Ermolenko MS, Yashunsky DV, Kochetkov NK (1991) Tetrahedron 47:2291

    Article  CAS  Google Scholar 

  28. Sviridov AF, Borodkin VS, Ermolenko MS, Yashunsky DV, Kochetkov NK (1991) Tetrahedron 47:2317

    Article  CAS  Google Scholar 

  29. Hikota M, Tone H, Horita K, Yonemitsu O (1990) J Org Chem 55:7

    Article  CAS  Google Scholar 

  30. Hikota M, Tone H, Horita K, Yonemitsu O (1990) Tetrahedron 46:4613

    Article  CAS  Google Scholar 

  31. Martin SF, Hida T, Kym PR, Loft M, Hodgson A (1997) J Am Chem Soc 119:3193

    Article  CAS  Google Scholar 

  32. Hergenrother PJ, Hodgson A, Judd AS, Lee WC, Martin SF (2003) Angew Chem Int Ed 42:3278

    Article  CAS  Google Scholar 

  33. Evans DA, Kim AS (1997) Tetrahedron Lett 38:53

    Article  CAS  Google Scholar 

  34. Evans DA, Kim AS, Metternich R, Novack VJ (1998) J Am Chem Soc 120:5921

    Article  CAS  Google Scholar 

  35. Muri D, Lohse-Fraefel N, Carreira EM (2005) Angew Chem Int Ed 44:4036

    Article  CAS  Google Scholar 

  36. Toshima K, Tatsuta K, Kinoshita M (1986) Tetrahedron Lett 27:4741

    Article  CAS  Google Scholar 

  37. Toshima K, Tatsuta K, Kinoshita M (1988) Bull Chem Soc Jpn 61:2369

    Article  CAS  Google Scholar 

  38. Nakamura H, Arata K, Wakamatsu T, Ban Y, Shibasaki M (1990) Chem Pharm Bull 38:2435

    CAS  Google Scholar 

  39. Seebach D, Chow H-F, Jackson RFW, Lawson K, Sutter MA, Thaisrivongs S, Zimmermann J (1985) J Am Chem Soc 107:5292

    Article  CAS  Google Scholar 

  40. Seebach D, Chow H-F, Jackson RFW, Sutter MA, Thaisrivongs S, Zimmermann J (1986) Liebigs Ann Chem 1281

    Google Scholar 

  41. Ziegler FE, Tung JS (1991) J Org Chem 56:6530

    Article  CAS  Google Scholar 

  42. Evans DA, Fitch DM (1997) J Org Chem 62:454

    Article  CAS  Google Scholar 

  43. Paterson I, Man J (1997) Tetrahedron Lett 38:695

    Article  CAS  Google Scholar 

  44. Paterson I, Lombart HG, Allerton C (1999) Org Lett 1:19

    Article  CAS  Google Scholar 

  45. Nakata M, Osumi T, Ueno A, Kimura T, Tamai T, Tatsuta K (1991) Tetrahedron Lett 32:6015

    Article  CAS  Google Scholar 

  46. Nakata M, Osumi T, Ueno A, Kimura T, Tamai T, Tatsuta K (1992) Bull Chem Soc Jpn 65:2974

    Article  CAS  Google Scholar 

  47. Eshelman JE, Epps JL, Kallmerten J (1993) Tetrahedron Lett 34:749

    Article  CAS  Google Scholar 

  48. Carter KD, Panek JS (2004) Org Lett 6:55

    Article  CAS  Google Scholar 

  49. Baker R, Castro JL (1989) J Chem Soc Chem Commun 378

    Google Scholar 

  50. Baker R, Castro JL (1990) J Chem Soc Perkin Trans 1 47

    Google Scholar 

  51. Evans DA, Miller SJ, Ennis MD, Ornstein PL (1992) J Org Chem 57:1067

    Article  CAS  Google Scholar 

  52. Evans DA, Miller SJ, Ennis MD (1993) J Org Chem 58:471

    Article  CAS  Google Scholar 

  53. Panek JS, Xu F (1995) J Am Chem Soc 117:10587

    Article  CAS  Google Scholar 

  54. Panek JS, Xu F, Rondon AC (1998) J Am Chem Soc 120:4113

    Article  CAS  Google Scholar 

  55. Coutts SJ, Wittman MD, Kallmerten J (1990) Tetrahedron Lett 31:4301

    Article  CAS  Google Scholar 

  56. Coutts SJ, Kallmerten J (1990) Tetrahedron Lett 31:4305

    Article  CAS  Google Scholar 

  57. Martin SF, Dodge JA, Burgess LE, Hartmann M (1992) J Org Chem 57:1070

    Article  CAS  Google Scholar 

  58. Martin SF, Dodge JA, Burgess LE, Limberakis C, Hartmann M (1996) Tetrahedron 52:3229

    Article  CAS  Google Scholar 

  59. Marshall JA, Sedrani R (1991) J Org Chem 56:5496

    Article  CAS  Google Scholar 

  60. Tatsuta K, Itoh M, Hirama R, Araki N, Kitagawa M (1997) Tetrahedron Lett 38:583

    Article  CAS  Google Scholar 

  61. Chida N, Takeoka J, Tsutsumi N, Ogawa S (1995) J Chem Soc Chem Commun 793

    Google Scholar 

  62. Chida N, Takeoka J, Ando K, Tsutsumi N, Ogawa S (1997) Tetrahedron 53:16287

    Article  CAS  Google Scholar 

  63. Corey EJ, Reichard GA (1992) J Am Chem Soc 114:10677

    Article  CAS  Google Scholar 

  64. Corey EJ, Reichard GA, Kania R (1993) Tetrahedron Lett 34:6977

    Article  CAS  Google Scholar 

  65. Corey EJ, Li W, Nagamitsu T (1998) Angew Chem Int Ed Engl 37:1676

    Article  CAS  Google Scholar 

  66. Corey EJ, Li W, Reichard GA (1998) J Am Chem Soc 120:2330

    Article  CAS  Google Scholar 

  67. Sunazuka T, Nagamitsu T, Tatsuzaki K, Tanaka H, Omura S, Smith III AB (1993) J Am Chem Soc 115:5302

    Article  CAS  Google Scholar 

  68. Nagamitsu T, Sunazuka T, Tanaka H, Omura S, Sprengeler PA, Smith III AB (1996) J Am Chem Soc 118:3584

    Article  CAS  Google Scholar 

  69. Uno H, Baldwin JE, Russell AT (1994) J Am Chem Soc 116:2139

    Article  CAS  Google Scholar 

  70. Panek JS, Masse CE (1999) Angew Chem Int Ed 38:1093

    Article  CAS  Google Scholar 

  71. Ooi H, Ishibashi N, Iwabuchi Y, Ishihara J, Hatakeyama S (2004) J Org Chem 69:7765

    Article  CAS  Google Scholar 

  72. Fukuda N, Sasaki K, Sastry TVRS, Kanai M, Shibasaki M (2006) J Org Chem 71:1220

    Article  CAS  Google Scholar 

  73. Balskus EP, Jacobsen EN (2006) J Am Chem Soc 128:6810

    Article  CAS  Google Scholar 

  74. Oikawa H, Oikawa M, Ueno T, Ichihara A (1994) Tetrahedron Lett 35:4809

    Article  CAS  Google Scholar 

  75. Oikawa M, Ueno T, Oikawa H, Ichihara A (1995) J Org Chem 60:5048

    Article  CAS  Google Scholar 

  76. Jiang Y, Ichikawa Y, Isobe M (1995) Synlett 285

    Google Scholar 

  77. Ichikawa Y, Tsuboi K, Jiang Y, Naganawa A, Isobe M (1995) Tetrahedron Lett 36:7101

    Article  CAS  Google Scholar 

  78. Jiang Y, Ichikawa Y, Isobe M (1997) Tetrahedron 53:5103

    Article  CAS  Google Scholar 

  79. Tsuboi K, Ichikawa Y, Naganawa A, Isobe M, Ubukata M, Isono K (1997) Tetrahedron 53:5083

    Article  CAS  Google Scholar 

  80. Tsuboi K, Ichikawa Y, Jiang Y, Naganawa A, Isobe M (1997) Tetrahedron 53:5123

    Article  CAS  Google Scholar 

  81. Nakamura S, Shibasaki M (1994) Tetrahedron Lett 35:4145

    Article  CAS  Google Scholar 

  82. Shimizu S, Nakamura S, Nakada M, Shibasaki M (1996) Tetrahedron 52:13363

    Article  CAS  Google Scholar 

  83. Corey EJ, Weigel LO, Chamberlin AR, Lipshutz B (1980) J Am Chem Soc 102:1439

    Article  CAS  Google Scholar 

  84. Sheppeck JE, Liu W, Chamberlin AR (1997) J Org Chem 62:387

    Article  CAS  Google Scholar 

  85. Marshall JA, Yanik MM (2001) J Org Chem 66:1373

    Article  CAS  Google Scholar 

  86. Maurer KW, Armstrong RW (1996) J Org Chem 61:3106

    Article  CAS  Google Scholar 

  87. Nagumo S, Arai T, Akita H (1997) Tetrahedron Lett 38:5165

    Article  CAS  Google Scholar 

  88. Jones TK, Mills SG, Reamer RA, Askin D, Desmond R, Volante RP, Shinkai I (1989) J Am Chem Soc 111:1157

    Article  CAS  Google Scholar 

  89. Jones TK, Reamer RA, Desmond R, Mills SG (1990) J Am Chem Soc 112:2998

    Article  CAS  Google Scholar 

  90. Villalobos A, Danishefsky SJ (1989) J Org Chem 54:13

    Article  Google Scholar 

  91. Linde II RG, Egbertson M, Coleman RS, Jones AB, Danishefsky SJ (1990) J Org Chem 55:2771

    Article  CAS  Google Scholar 

  92. Villalobos A, Danishefsky SJ (1990) J Org Chem 55:2776

    Article  CAS  Google Scholar 

  93. Jones AB, Villalobos A, Linde II RG, Danishefsky SJ (1990) J Org Chem 55:2786

    Article  CAS  Google Scholar 

  94. Schreiber SL, Sammakia T, Uehling DE (1989) J Org Chem 54:15

    Article  CAS  Google Scholar 

  95. Nakatsuka M, Ragan JA, Sammakia T, Smith DB, Uehling DE, Schreiber SL (1990) J Am Chem Soc 112:5583

    Article  CAS  Google Scholar 

  96. Ireland RE, Gleason JL, Gegnas LD, Highsmith TK (1996) J Org Chem 61:6856

    Article  CAS  Google Scholar 

  97. Ireland RE, Liu L, Roper TD (1997) Tetrahedron 53:13221

    Article  CAS  Google Scholar 

  98. Ireland RE, Liu L, Roper TD, Gleason JL (1997) Tetrahedron 53:13257

    Article  CAS  Google Scholar 

  99. Smith III AB, Hale KJ (1989) Tetrahedron Lett 30:1037

    Article  CAS  Google Scholar 

  100. Smith III AB, Hale KJ, Laakso LM, Chen K, Ri'era A (1989) Tetrahedron Lett 30:6963

    Article  CAS  Google Scholar 

  101. Smith III AB, Chen K, Robinson DJ, Laakso LM, Hale KJ (1994) Tetrahedron Lett 35:4271

    Article  CAS  Google Scholar 

  102. Rosenthal A, Catsoulacos P (1969) Can J Chem 47:2747

    CAS  Google Scholar 

  103. Jarosz S, Hicks DR, Fraser-Reid B (1982) J Org Chem 47:935

    Article  CAS  Google Scholar 

  104. Rama Rao AV, Chakraborty TK, Reddy KL (1990) Tetrahedron Lett 31:1439

    Article  Google Scholar 

  105. Rama Rao AV, Chakraborty TK, Reddy KL (1991) Tetrahedron Lett 32:1251

    Article  Google Scholar 

  106. Maier ME, Haller B-U, Stumpf R, Fischer H (1993) Synlett 863

    Google Scholar 

  107. Gu R-L, Sih CJ (1990) Tetrahedron Lett 31:3283

    Article  CAS  Google Scholar 

  108. Zheng W, Seletsky BM, Palme MH, Lydon PJ, Singer LA, Chase CE, Lemelin CA, Shen Y, Davis H, Tremblay L, Towle MJ, Salvato KA, Wels BF, Aalfs KA, Kishi Y, Littlefield BA, Yu MJ (2004) Bioorg Med Chem Lett 14:5551

    Article  CAS  Google Scholar 

  109. Towle MJ, Salvato KA, Budrow J, Wels BF, Kuznetsov G, Aalfs KK, Welsh S, Zheng W, Seletsky BM, Palme MH, Habgood GJ, Singer LA, DiPietro LV, Wang Y, Chen JJ, Quincy DA, Davis A, Yoshimatsu K, Kishi Y, Yu MJ, Littlefield BA (2001) Cancer Res 61:1013

    CAS  Google Scholar 

  110. Kuznetsov G, Towle MJ, Cheng H, Kawamura T, TenDyke K, Liu D, Kishi Y, Yu MJ, Littlefield BA (2004) Cancer Res 64:5760

    Article  CAS  Google Scholar 

  111. Aicher TD, Kishi Y (1987) Tetrahedron Lett 28:3463

    Article  CAS  Google Scholar 

  112. Aicher TD, Buszek KR, Fang FG, Forsyth CJ, Jung SH, Kishi Y, Scola PM (1992) Tetrahedron Lett 33:1549

    Article  CAS  Google Scholar 

  113. Buszek KR, Fang FG, Forsyth CJ, Jung SH, Kishi Y, Scola PM, Yoon SK (1992) Tetrahedron Lett 33:1553

    Article  CAS  Google Scholar 

  114. Fang FG, Kishi Y, Matelich MC, Scola PM (1992) Tetrahedron Lett 33:1557

    Article  CAS  Google Scholar 

  115. Aicher TD, Buszek KR, Fang FG, Forsyth CJ, Jung SH, Kishi Y, Matelich MC, Scola PM, Spero DM, Yoon SK (1992) J Am Chem Soc 114:3162

    Article  CAS  Google Scholar 

  116. Kishi Y (1992) Pure Appl Chem 64:343

    Article  CAS  Google Scholar 

  117. Duan JJW, Kishi Y (1993) Tetrahedron Lett 34:7541

    Article  CAS  Google Scholar 

  118. Stamos DP, Kishi Y (1996) Tetrahedron Lett 37:8643

    Article  CAS  Google Scholar 

  119. Stamos DP, Chen SS, Kishi Y (1997) J Org Chem 62:7552

    Article  CAS  Google Scholar 

  120. Wong MYH, Gray GR (1978) J Am Chem Soc 100:3548

    Article  CAS  Google Scholar 

  121. Vekemans JAJM, Boerekamp J, Godefroi EF, Chittenden GJF (1985) Recl Trav Chim Pays-Bas 104:266

    Article  CAS  Google Scholar 

  122. Vekemans JAJM, de Bruyn RGM, Caris RCHM, Kokx AJPM, Konings JJHG, Godefroi EF, Chittenden GJF (1987) J Org Chem 52:1093

    Article  CAS  Google Scholar 

  123. Vekemans JAJM, Franken GAM, Dapperens CWM, Godefroi EF, Chittenden GJF (1988) J Org Chem 53:627

    Article  CAS  Google Scholar 

  124. Kim S, Salomon RG (1989) Tetrahedron Lett 30:6279

    Article  CAS  Google Scholar 

  125. Cooper AJ, Salomon RG (1990) Tetrahedron Lett 31:3813

    Article  CAS  Google Scholar 

  126. DiFranco E, Ravikumar VT, Salomon RG (1993) Tetrahedron Lett 34:3247

    Article  CAS  Google Scholar 

  127. Cooper AJ, Pan W, Salomon RG (1993) Tetrahedron Lett 34:8193

    Article  CAS  Google Scholar 

  128. Horita K, Hachiya S, Nagasawa M, Hikota M, Yonemitsu O (1994) Synlett 38

    Google Scholar 

  129. Horita K, Nagasawa M, Hachiya S, Yonemitsu O (1994) Synlett 40

    Google Scholar 

  130. Horita K, Sakurai Y, Nagasawa M, Hachiya S, Yonemitsu O (1994) Synlett 43

    Google Scholar 

  131. Horita K, Sakurai Y, Nagasawa M, Maeno K, Hachiya S, Yonemitsu O (1994) Synlett 46

    Google Scholar 

  132. Horita K, Hachiya S, Ogihara K, Yoshida Y, Nagasawa M, Yonemitsu O (1996) Heterocycles 42:99

    Article  CAS  Google Scholar 

  133. Horita K, Hachiya S, Yamazaki T, Naitou T, Uenishi J, Yonemitsu O (1997) Chem Pharm Bull 45:1265

    CAS  Google Scholar 

  134. Horita K, Sakurai Y, Nagasawa M, Yonemitsu O (1997) Chem Pharm Bull 45:1558

    CAS  Google Scholar 

  135. Horita K, Nagasawa M, Hachiya S, Sakurai Y, Yamazaki T, Uenishi J, Yonemitsu O (1997) Tetrahedron Lett 38:8965

    Article  CAS  Google Scholar 

  136. Horita K, Nagasawa M, Sakurai Y, Yonemitsu O (1998) Chem Pharm Bull 46:1199

    CAS  Google Scholar 

  137. Burke SD, Jung KW, Lambert WT, Phillips JR, Klovning JJ (2000) J Org Chem 65:4070

    Article  CAS  Google Scholar 

  138. Austad BC, Hart AC, Burke SD (2002) Tetrahedron 58:2011

    Article  CAS  Google Scholar 

  139. Jiang L, Martinelli JR, Burke SD (2003) J Org Chem 68:1150

    Article  CAS  Google Scholar 

  140. Lambert WT, Hanson GH, Benayoud F, Burke SD (2005) J Org Chem 70:9382

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, 223-8522, Japan

    Masaya Nakata

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  1. Masaya Nakata
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Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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Nakata, M. (2008). Monosaccharides as Chiral Pools for the Synthesis of Complex Natural Compounds. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_21

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