Total Synthesis of the Polycyclic Fungal Metabolite (±)-Communesin F

被引:103
作者
Liu, Peng [1 ]
Seo, Jae Hong [1 ]
Weinreb, Steven M. [1 ]
机构
[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
alkaloids; Heck reactions; natural products; nitrogen heterocycles; total synthesis; PENICILLIUM-EXPANSUM LINK; BIOMIMETIC APPROACH; COMMUNESIN; PEROPHORAMIDINE; NOMOFUNGIN; ALKALOIDS; BIOSYNTHESIS;
D O I
10.1002/anie.200906818
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) What the Heck: The heptacyclic fungal alkaloid communesin F was the target of a total synthesis featuring a rare example of an intramolecular Heck cyclization of a tetrasubstituted alkene, a reductive cyclization of an N-Boc aniline, a stereoselective C allylation of a lactam, and an azide reduction/N-Boc-d-lactam ring opening sequence (see scheme, BOM=benzyloxymethyl). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2000 / 2003
页数:4
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