Enantioselective total synthesis of (+)-obtusenyne

被引：64

作者：

Crimmins, MT ^{[1
]}

Powell, MT

机构：

[1] Univ N Carolina, Dept Chem Venable, Chapel Hill, NC 27515 USA

[2] Univ N Carolina, Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 25期

关键词：

D O I：

10.1021/ja029956v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A total synthesis of the laurencia metabolite (+)-obtusenyne has been completed. The key steps include a Sharpless kinetic resolution and an asymmetric glycolate alkylation to establish the stereogenic centers adjacent to the ether linkage and a ring-closing metathesis reaction to construct the nine-membered ether without the aid of a cyclic conformational constraint. The synthesis was completed in 20 linear steps from commercially available 1,5-hexadiene-3-ol.

引用

页码：7592 / 7595

页数：4

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