Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions

被引：109

作者：

Ramachandran, PV ^{[1
]}

Reddy, MVR ^{[1
]}

Brown, HC ^{[1
]}

机构：

[1] Purdue Univ, HC Brown & RB Wetherill Labs Chem, W Lafayette, IN 47907 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 05期

关键词：

asymmetric synthesis; allylboration; metathesis;

D O I：

10.1016/S0040-4039(99)02130-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B-allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

引用

页码：583 / 586

页数：4

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