Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (-)-(6S,2′S)-epi cryptocaryalactone

被引：31

作者：

Sabitha, Gowravaram ^{[1
]}

Bhaskar, V. ^{[1
]}

Reddy, S. Siva Sankara ^{[1
]}

Yadav, J. S. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2008年 / 64卷 / 44期

关键词：

alpha; beta-Unsaturated delta-lactone; Base catalyzed conjugate addition; Z-Wittig olefination; Stereoselective reduction; cis Wittig olefination; 1,3-Polyol;

D O I：

10.1016/j.tet.2008.08.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (+)-(6R,2'S)-cryptocaryalactone and (-)-(6S,2'S)-epi cryptocaryalactone is reported based on stereoselective reduction of delta-hydroxy beta-keto ester to install 1,3-polyol system, cis Wittig olefination, and lactonization as the key steps. The synthesis of (-)-(6S,2'S)-epi cryptocaryalactone is also reported using syn-benzylidene acetal formation and a preferential Z-Wittig olefination reaction and lactonization as the key steps. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10207 / 10213

页数：7

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