Biomimetic total synthesis of (±)-yezo′otogirin A

被引：17

作者：

Lam, Hiu C. ^{[1
]}

Kuan, Kevin K. W. ^{[1
]}

George, Jonathan H. ^{[1
]}

机构：

[1] Univ Adelaide, Dept Chem, Adelaide, SA 5005, Australia

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 16期

基金：

澳大利亚研究理事会;

关键词：

POLYCYCLIC POLYPRENYLATED ACYLPHLOROGLUCINOLS; MANGANESE(III) ACETATE; RADICAL CYCLIZATIONS; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; GAMMA-LACTONES; FORCE-FIELD;

D O I：

10.1039/c4ob00186a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. The synthesis showcases the ability of biomimetic radical cyclizations to generate complex natural products from unprotected intermediates.

引用

页码：2519 / 2522

页数：4

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