Total synthesis of pederin

被引：61

作者：

Jewett, John C. ^{[1
]}

Rawal, Viresh H. ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 34期

关键词：

curtius rearrangement; diastereoselectivity; Mukaiyama-Michael reaction; natural products; total synthesis;

D O I：

10.1002/anie.200701677

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Blisteringly fast: The potent cytotoxic blistering agent pederin has been synthesized (see scheme). The synthesis is diastereoselective and concise (just 12 steps for the longest linear sequence), and features a formal hetero-Diels-Alder reaction of a hindered diene, a Mukaiyama-Michael reaction to set two additional stereocenters, and a Curtius rearrangement to stereospecifically introduce the aminal functionality. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6502 / 6504

页数：3

共 30 条

[11] STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-PEDERINE [J].

MATSUDA, F ;

TOMIYOSHI, N ;

YANAGIYA, M ;

MATSUMOTO, T .

TETRAHEDRON, 1988, 44 (23) :7063-7080

[12]

MATSUMOTO T, 1968, TETRAHEDRON LETT, V9, P6297

[13]

Narquizian R, 2000, E SCHERING RES FDN W, V32, P25

[14]

Netolitzky F., 1919, Za angew Ent Berlin, V5, P252

[15] Blister beetles and the ten plagues [J].

Norton, SA ;

Lyons, C .

LANCET, 2002, 359 (9321) :1950-1950

[16]

PAVAN M., 1953, PHYSIOL COMPARATA ET OECOL, V3, P307

[17]

Pavan M, 1952, MEM SOC ENTOMOL ITAL, V31, P67

[18] Exploring the chemistry of uncultivated bacterial symbionts: Antitumor polyketides of the pederin family [J].

Piel, J ;

Butzke, D ;

Fusetani, N ;

Hui, DQ ;

Platzer, M ;

Wen, GP ;

Matsunaga, S .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (03) :472-479

[19]

RADEMACHER CMK, 1997, THESIS OHIO STATE U

[20]

Richter A, 1997, ANTI-CANCER DRUG DES, V12, P217

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