HIGHLY DIASTEREOSELECTIVE ALDOL REACTIONS OF COBALT-COMPLEXED AND UNCOMPLEXED PROPYNALS WITH AN O-SILYL KETENE O,S-ACETAL - HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (+/-)-BLASTMYCINONE AND ITS 3 DIASTEREOISOMERS FROM 3-(TRIMETHYLSILYL)PROPYNAL

被引：44

作者：

MUKAI, C ^{[1
]}

KATAOKA, O ^{[1
]}

HANAOKA, M ^{[1
]}

机构：

[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA,ISHIKAWA 920,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 11期

关键词：

D O I：

10.1021/jo00063a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total syntheses of (+/-)-blastmycinone (2) and its three diastereoisomers (3-5) are described. The syntheses involve highly stereoselective aldol reactions of cobalt-complexed propynal 6 and uncomplexed propynal 7 with O-silyl ketene O,S-acetal 8, which possesses an n-butyl tether, under Mukaiyama conditions. (+/-)-Blastmycinone (2) and its 2-epimer 3 were stereoselectively synthesized through chelation-controlled reduction, whereas (+/-)-3-epi- and 4-epiblastmycinone (5 and 4) were obtained in a highly stereocontrolled manner with bromolactonization as a key step.

引用

页码：2946 / 2952

页数：7

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