Total Synthesis of Aspeverin via an Iodine(III)-Mediated Oxidative Cyclization

被引：20

作者：

Levinson, Adam M. ^{[1
]}

机构：

[1] Mem Sloan Kettering Canc Ctr, Bioorgan Chem Lab, Tri Inst PhD Program Chem Biol, New York, NY 10065 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 18期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOCONTROLLED TOTAL-SYNTHESIS; MARINE-DERIVED FUNGUS; 2,3-DISUBSTITUTED INDOLES; CITRINADIN-A; ALKALOIDS; CONCISE; DERIVATIVES; CHEMISTRY; REVISION;

D O I：

10.1021/ol5024163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of aspeverin, a prenylated indole alkaloid isolated from Aspergillus versicolor in 2013, is described. Key steps utilized to assemble the core structure of the target include a highly diastereoselective Diels-Alder reaction, a Curtius rearrangement, and a unique strategy for installation of the geminal dimethyl group. A novel iodine(III)-initiated cyclization was then used to install the bicyclic urethane linkage distinctive to the natural product.

引用

页码：4904 / 4907

页数：4

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