ACETOXYFULVENE SYNTHESIS OF PROSTAGLANDINS .1. SYNTHESIS OF THE COREY ALDEHYDE

被引：32

作者：

BROWN, ED

CLARKSON, R

LEENEY, TJ

ROBINSON, GE

机构：

[1] I.C.I. Limited, Pharmaceuticals Division, Mereside, Macclesfield, Cheshire SK10 4TG, Alderley Park

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1978年 / 12期

关键词：

D O I：

10.1039/p19780001507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short and practical alternative synthesis of the Corey aldehyde (2), a key intermediate in prostaglandin synthesis, is described. 6-Acetoxyfulvene (7) underwent a Diels-Alder reaction with 2-chloroacrylonitrile to give 7-acetoxy-methylene-2-chlorobicyclo[2.2.1]hept-5-ene-2-carbonitrile (8) which was converted sequentially into 2-chloro-7-anti-formylbicyclo[2.2.1]hept-5-ene-2-carbonitrile (10) and its 7-syn-isomer (11). The factors controlling the stereochemistry at C(7) in the anti- and syn-aldehydes (10) and (11) are discussed in detail.

引用

页码：1507 / 1511

页数：5

共 18 条

[1] 16-ARYLOXYPROSTAGLANDINS - NEW CLASS OF POTENT LUTEOLYTIC AGENT
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[6] REAGENTS FOR STEREOSELECTIVE CARBONYL REDUCTION - IMPROVED SYNTHETIC ROUTE TO PRIMARY PROSTAGLANDINS
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[7] STEREO-CONTROLLED SYNTHESIS OF PROSTAGLANDINS F2ALPHA AND E2 (DL)
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[8] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF POTENT, SELECTIVE, LUTEOLYTIC PROSTAGLANDINS
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[9] POTENT LUTEOLYTIC AGENTS RELATED TO PROSTAGLANDIN-F2ALPHA
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[10] FIESER LF, 1976, REAGENTS ORGANIC SYN, P146

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