Total Synthesis of Jerangolid A

被引：39

作者：

Hanessian, Stephen ^{[1
]}

Focken, Thilo ^{[1
]}

Oza, Rupal ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

FUNCTIONALIZED ALKENYLMAGNESIUM REAGENTS; INTRAMOLECULAR OXYPALLADATION REACTION; SORANGIUM-CELLULOSUM; STEREOSELECTIVE-SYNTHESIS; 1,3-CHIRALITY TRANSFER; POLYKETIDE AMBRUTICIN; OLEFINATION; TETRAHYDROPYRANS; PHOSPHONAMIDES; CONDENSATION;

D O I：

10.1021/ol101103q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the antifungal polyketide jerangolid A has been accomplished. Starting with the readily available (R)-Roche ester and (S)-glycidol as chirons, the synthesis involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization for the construction of the dihydropyran subunit. The lactone segment was built through a tandem NaOMe conjugate addition-lactonization reaction, and further functionalized through a sequence consisting of iodination, I-Mg exchange, and hydroxymethylation. Other key steps in the synthesis featured a novel application of a phosphonamide-anion based olefination and a Julia-Kocienski reaction.

引用

页码：3172 / 3175

页数：4

共 44 条

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