STEREOSELECTIVE SYNTHESES OF LIGNANS UTILIZING CYANOHYDRINS

被引：10

作者：

OHMIZU, H ^{[1
]}

IWASAKI, T ^{[1
]}

机构：

[1] PHARMACOL RES LAB, TODA, SAITAMA 335, JAPAN

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 1995年 / 53卷 / 07期

关键词：

LIGNAN; CYANOHYDRIN; 3-COMPONENT REACTION; STEREOSELECTIVE SYNTHESIS; ALDOL REACTION; ASYMMETRIC SYNTHESIS; MICHAEL ADDITION;

D O I：

10.5059/yukigoseikyokaishi.53.593

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The comprehensive synthesis of a variety of lignans based on our conceptually new synthetic strategy is described. Lignans were synthesized effectively by using the key intermediate 2. The compound 2 was synthesized in a stereoselective manner by the Michael addition of the O-TBS cyanohydrin to 2-butenolide, followed by the aldol reaction of the resulting enolate with an aromatic aldehyde. The key intermediate 2 was converted into: lignans of the aryltetralin series including podophyllotoxin stereoselectively; 1-arylnaphthalene and 1-aryl 4-hydroxynaphihalene lignans in a one-pot procedure by the acid-catalyzed cyclization and the aromatization-lactonization, respectively; lignans of the furofuran and bislactone-type furofuran series by the stereoselective intramolecular cyclization. Finally, we describe the asymmetric synthesis of lignans utilizing the chiral benzyl-lactones 68 and 73 as key intermediates which were synthesized via the Michael addition of the cyanohydrin 15 to chiral alpha,beta-unsaturated esters 65 and 71.

引用

页码：593 / 603

页数：11