Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C

被引：40

作者：

Jessen, Henning J. ^{[1
]}

Schumacher, Andreas ^{[1
]}

Schmid, Fabian ^{[1
]}

Pfaltz, Andreas ^{[1
]}

Gademann, Karl ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 16期

基金：

瑞士国家科学基金会;

关键词：

CHIRAL BUILDING-BLOCKS; ASYMMETRIC HYDROGENATION; ENTOMOPATHOGENIC FUNGI; ORGANIC-SYNTHESIS; PYRIDOVERICIN; PYRIDOMACROLIDIN; METABOLITES; STRATEGY; ACIDS;

D O I：

10.1021/ol201692h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silyl-protected (R)-methyl 2-(hydroxymethyl)butanoate was obtained by an enantioselective Ir-catalyzed hydrogenation In high yield and selectivity. Elaboration of this building block via Takai and Stille reactions gave a protected hydroxy polyene chain, which was coupled to a 5-hydroxyphenyl-4-hydroxy-2-pyridone derivative by a modified Horner-Wadsworth-Emmons reaction. Deprotection gave synthetic (+)-torrublelione C, which led to the assignment of the configuration of the natural product as (R).

引用

收藏

页码：4368 / 4370

页数：3

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