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
收藏
页码：2422 / 2429
页数：8
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