Enantioselective Synthesis of (+)-Malbrancheamide B

被引：30

作者：

Laws, Stephen W. ^{[1
]}

Scheerer, Jonathan R. ^{[1
]}

机构：

[1] Coll William & Mary, Dept Chem, Williamsburg, VA 23187 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

关键词：

BIOMIMETIC TOTAL-SYNTHESIS; DIELS-ALDER CYCLOADDITION; BIOSYNTHETIC INCORPORATION; MALBRANCHEAMIDE-B; CONCISE SYNTHESIS; NATURAL-PRODUCTS; INDOLE ALKALOIDS; STEPHACIDIN; PARAHERQUAMIDES; BREVIANAMIDES;

D O I：

10.1021/jo3026059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric total synthesis of the chlorinated [2.2.2]-diazabicyclic indole alkaloid (+)-malbrancheamide B is reported. Key to the synthesis is a domino reaction sequence that employs an aldol condensation, alkene isomerization, and intramolecular Diels-Alder cycloaddition. Diastereofacial selection between the azadiene stereofaces is enforced with a chiral aminal auxiliary. A formal 7-step (longest linear route) synthesis of (+/-)-malbrancheamide B is also reported.

引用

页码：2422 / 2429

页数：8

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