Total Synthesis of Muricadienin, the Putative Key Precursor in the Solamin Biosynthesis

被引：26

作者：

Adrian, Juliane ^{[1
]}

Stark, Christian B. W. ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, Fachbereich Chem, D-20146 Hamburg, Germany

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 22期

关键词：

MITOCHONDRIAL COMPLEX-I; ANNONA-MURICATA SEEDS; MONO-THF ACETOGENINS; CIS-SOLAMIN; OXIDATIVE CYCLIZATION; BIOMIMETIC SYNTHESIS; NATURAL-PRODUCTS; HERONAPYRROLE C; RECENT PROGRESS; DIOLS;

D O I：

10.1021/ol502849y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of muricadienin, the unsaturated putative precursor in the biosynthesis of trans- and cis-solamin is described. Key steps in the synthesis are a chemoselective hydroboration, a Z-selective Wittig reaction, and a Fries rearrangement for introducing the terminal alpha-substituted butenolide. Thus, muricadienin can be synthesized in 11 steps from commercially available starting materials in 42% overall yield.

引用

页码：5886 / 5889

页数：4

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