Total Synthesis of Grandisine D

被引：36

作者：

Kurasaki, Haruaki ^{[2
]}

Okamoto, Iwao ^{[1
]}

Morita, Nobuyoshi ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Tokyo 1948543, Japan

[2] Kyorin Pharmaceut Co Ltd, Discovery Res Labs, Nogi, Tochigi 3290114, Japan

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 05期

关键词：

BAYLIS-HILLMAN REACTION; LEWIS-BASE ORGANOCATALYST; TREE ELAEOCARPUS-GRANDIS; CHIRAL BRONSTED ACIDS; ABSOLUTE-CONFIGURATION; INDOLIZIDINE ALKALOIDS; ASYMMETRIC-SYNTHESIS; CHEMISTRY; IONS;

D O I：

10.1021/ol900032h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of grandisine D (5) was achieved by a Bronsted acid mediated Morita-Baylis-Hillman (MBH) ring-closure reaction and stereoselective aldol condensation with (S)-5-methylcyclohexenone (9) as key steps. The MBH approach was also applicable for the construction of the aza-fused bicyclic systems of pyrrolizidine and stemona alkaloids.

引用

页码：1179 / 1181

页数：3

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