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
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
收藏
页码:5886 / 5889
页数:4
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