Total synthesis of the potent antitumor polyketide (-)-callystatin A

被引：56

作者：

Dias, LC ^{[1
]}

Meira, PRR ^{[1
]}

机构：

[1] UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 12期

关键词：

D O I：

10.1021/jo050352u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly convergent and efficient total synthesis of the potent antitumor polyketide (-)-callystatin A is described. The synthesis required 19 steps from N-propionyl oxazolidinone 23 and produced the desired product in 3.5% overall yield.

引用

页码：4762 / 4773

页数：12

共 67 条

[1] Convenient preparations of (diphenylphosphono)acetic and esters and the comparison of the Z-selectivities of their Horner-Wadsworth-Emmons reaction with aldehydes depending on the ester moiety [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8406-8408

[2] Z-selective Horner-Wadsworth-Emmons reaction of ethyl (diarylphosphono)acetates using sodium iodide and DBU [J].

Ando, K ;

Oishi, T ;

Hirama, M ;

Ohno, H ;

Ibuka, T .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4745-4749

[3] Z-selective Horner-Wadsworth-Emmons reaction of α-substituted ethyl (diarylphosphono)acetates with aldehydes [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8411-8416

[4] Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates [J].

Ando, K .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :1934-1939

[5] Stereoselective synthesis of functionalized trisubstituted olefins via palladium(0)-catalyzed cross-coupling reaction [J].

Arefolov, A ;

Langille, NF ;

Panek, JS .

ORGANIC LETTERS, 2001, 3 (21) :3281-3284

[6] Determination of the relative and absolute stereochemistry of fostriecin (CI-920) [J].

Boger, DL ;

Hikota, M ;

Lewis, BM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1748-1753

[7] Total synthesis of fostriecin (CI-920) [J].

Boger, DL ;

Ichikawa, S ;

Zhong, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4161-4167

[8] TOTAL SYNTHESIS OF (+)-PHYLLANTHOCIN - INTRODUCTION OF INTRAMOLECULAR HYDROFORMYLATION FOR COMPLEX MOLECULE FUNCTIONALIZATION [J].

BURKE, SD ;

COBB, JE ;

TAKEUCHI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2138-2151

[9] Asymmetric total synthesis of callystatin A: Asymmetric aldol additions with titanium enolates of acyloxazolidinethiones [J].

Crimmins, MT ;

King, BW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9084-9085

[10] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

← 1 2 3 4 5 6 7 →