Total synthesis of (+)-isoschizandrin utilizing a samarium(II) iodide-promoted 8-endo ketyl-olefin cyclization

被引：99

作者：

Molander, GA ^{[1
]}

George, KM

Monovich, LG

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

[2] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo0347361

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(11) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and stereochemistry. In constructing (+)-isoschizandrin as a single atropisomer, the synthesis utilizes a kinetic resolution of a seven-membered lactone using a CBS-oxazaborolidine.

引用

页码：9533 / 9540

页数：8

共 58 条

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