Stereoselective synthesis of trans-fused tetrahydrofuran derivatives of 5H-dibenzo[a,d]cycloheptene

被引：9

作者：

Compernolle, F

Mao, H

Tahri, A

Kozlecki, T

Van der Eycken, E

Medaer, B

Hoornaert, GJ

机构：

[1] Katholieke Univ Leuven, Organ Synth Lab, B-3001 Heverlee, Belgium

[2] Johnson & Johnson Pharmaceut Res & Dev, Drug Evaluat, B-2340 Beerse, Belgium

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(02)00404-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The epoxides derived from 5H-dibenzo[a.d]cycloheptene and its 2-fluoro derivative were converted to trans-fused hydrofurans 4a.b (55 and 44% overall fields) via a five-step sequence. i.e. (i) epoxide ring opening using propargylmagnesium bromide. (ii) mercury(II)-induced cyclisation and in situ bromination to give the bromomethylene substituted hydrofurans, (iii, iv) acid catalysed hydration and stereoselective reduction of the hemiacetal intermediates, and (v) base promoted cyclisation. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3011 / 3015

页数：5

共 5 条

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