Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid

被引：11

作者：

Sammet, Benedikt ^{[1
]}

Radzey, Hanna ^{[1
]}

Neumann, Beate ^{[2
]}

Stammler, Hans-Georg ^{[2
]}

Sewald, Norbert ^{[1
]}

机构：

[1] Univ Bielefeld, Dept Chem Organ & Bioorgan Chem, D-33615 Bielefeld, Germany

[2] Univ Bielefeld, Dept Chem, D-33615 Bielefeld, Germany

来源：

SYNLETT | 2009年 / 03期

关键词：

asymmetric synthesis; bioorganic chemistry; epoxidations; lactones; natural products; POTENT CYTOTOXIC DEPSIPEPTIDE; ASYMMETRIC EPOXIDATION; ARENASTATIN-A; EFFICIENT;

D O I：

10.1055/s-0028-1087541

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unit A of cryptophycins is a delta-hydroxy acid with two or four stereogenic centers. The first synthesis of the unit A building block of cryptophycin-39 is based on a catalytic asymmetric Shi epoxidation of trans-styryl acetic acid followed by an in situ lactonization. The scope of this reaction has been investigated with respect to various beta,gamma-unsaturated carboxylic acids as substrates for the asymmetric synthesis of 4-hydroxy-5-phenyl-tetrahydrofuran-2-ones under Shi conditions.

引用

页码：417 / 420

页数：4

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