Synthesis of enantiopure dihydropyranones: Aldol-based ring expansion of dihydrofurans

被引：8

作者：

Donohoe, TJ

Raoof, A

Freestone, GC

Linney, ID

Cowley, A

Helliwell, M

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

[3] James Black Fdn, London SE24 9JE, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 18期

关键词：

D O I：

10.1021/ol0263595

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The stereoselective Birch reduction of 3-methyl-2-furoic acids using a readily available chiral auxilairy is described; by coupling this process to an oxidative cleavage/aldol ring closure sequence we were able to produce highly functionalized and enantiopure dihydropyranones in high yield. This sequence has ample flexibility built into it, either by the use of different electrophiles during reductive alkylation or by subsequent derivatization of the dihydropyranone after ring expansion.

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页码：3059 / 3062

页数：4

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