Stereoselective Synthesis of β-(Hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones

被引：53

作者：

Hodgson, David M. ^{[1
]}

Talbot, Eric P. A. ^{[1
]}

Clark, Barry P. ^{[2
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Eli Lilly & Co Ltd, LRL, Windlesham GU20 6PH, Surrey, England

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 10期

关键词：

ALPHA-METHYLENE BUTYROLACTONES; 1,2-OXIDIZED FUROFURAN LIGNAN; ONE-CARBON SOURCE; SESQUITERPENE LACTONES; GAMMA-BUTYROLACTONES; ORGANIC-SYNTHESIS; KEY INTERMEDIATE; DIBROMOMETHANE;

D O I：

10.1021/ol200711f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives beta-(hydroxymethylaryl/alkyl)-alpha-methylene-gamma-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (+/-)-hydroxymatalresinol (8) and (+/-)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization, respectively.

引用

页码：2594 / 2597

页数：4

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