Highly diastereoselective total synthesis of the anti-tumoral agent (±)-Spisulosine (ES285) from a Morita-Baylis-Hillman adduct

被引：43

作者：

Amarante, Giovanni W. ^{[1
]}

Cavallaro, Mayra ^{[1
]}

Coelho, Fernando ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, Lab Synth Nat Prod & Drugs, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 19期

基金：

巴西圣保罗研究基金会;

关键词：

ELECTROSPRAY-IONIZATION MASS; STEREOSELECTIVE-SYNTHESIS; MECHANISM; SPISULOSINE; CATALYSIS; REAGENT; ROUTE;

D O I：

10.1016/j.tetlet.2010.02.169

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We disclose herein a new approach for the highly diastereoselective total synthesis of the anti-tumoral agent (+/-)-Spisulosine. The synthesis was accomplished in seven steps with an overall yield of 10%. The key step involves the transformation of a Morita-Baylis-Hillman into an acyloin, which was subsequently used as substrate in a highly diastereoselective reductive amination reaction. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2597 / 2599

页数：3

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