Total Synthesis of (+)-Crocacin C Using Hidden Symmetry

被引：30
作者：
Candy, Mathieu [1 ]
Audran, Gerard [1 ]
Bienayme, Hugue [1 ]
Bressy, Cyril [1 ]
Pons, Jean-Marc [1 ]
机构：
[1] Aix Marseille Univ, Inst Sci Mol Marseille, CNRS, iSm2,Equipe STeReO,UMR 6263, F-13397 Marseille 20, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 05期
关键词：
STEREOSELECTIVE-SYNTHESIS; CHONDROMYCES-CROCATUS; NATURAL-PRODUCTS; CROCACIN; MYXOBACTERIA; CYCLIZATION; ALKYNES; ACCESS; ACIDS; TIN;
D O I：
10.1021/jo902582w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly convergent and protecting-group-free synthesis of (+)-crocacin C, featuring an enzymatic enantioselective desymmetrization of a meso-diol, a base-induced ring opening of a THP ring, and a one-pot hydrostannylation/Stille coupling as the key steps, is reported. The natural product was obtained in 11 steps and 22.3% overall yield starting from readily available oxabicycle 1. Finally, a unique enantioselective step, an enzymatic desymmetrization, revealed four stereogenic centers and created one in C4 of the THP furnishing the dense building block 4 with high enantioselectivity (ce >98%).
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收藏
页码：1354 / 1359
页数：6
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