A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides

被引：19

作者：

Davoust, Marion ^{[1
]}

Cantagrel, Frederic ^{[1
]}

Metzner, Patrick ^{[1
]}

Briere, Jean-Francois ^{[1
,2
,3
]}

机构：

[1] Univ Caen, Lab Chim Mol & Thioorgan, ENSICAEN, CNRS, F-14050 Caen, France

[2] IRCOF, INSA Rouen, F-76131 Mont St Aignan, France

[3] Univ Rouen, CNRS, UMR 6014, COBRA, F-76131 Mont St Aignan, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2008年 / 6卷 / 11期

关键词：

D O I：

10.1039/b802310g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic diastereoselective sulfonium ylide epoxidation of aldehydes furnished original vinyl epoxides, having an MBH backbone. These highly functionalised building blocks were used for a formal synthesis of the antibiotic conocandin, and opened up a stereodivergent route towards beta-hydroxy-alpha-methylene lactones, core units of naturally occurring compounds. Under acidic conditions, the oxiranes were mainly transformed, with moderate to good yields, into trans beta-hydroxy-alpha-methylene lactones. On the other hand, a user-friendly palladium-catalysed CO2 insertion and cyclisation sequence gave the cis beta-hydroxy-alpha-methylene lactone counterparts along with an interesting cis-trans equilibration of the pi-allyl intermediates.

引用

页码：1981 / 1993

页数：13

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