Synthesis enables a structural revision of the Mycobacterium tuberculosis-produced diterpene, edaxadiene

被引：19
作者：
Spangler, Jillian E. [1 ]
Carson, Cheryl A. [1 ]
Sorensen, Erik J. [1 ]
机构：
[1] Princeton Univ, Dept Chem, Frick Chem Lab, Princeton, NJ 08544 USA
来源：
CHEMICAL SCIENCE | 2010年 / 1卷 / 02期
基金：
加拿大自然科学与工程研究理事会; 美国国家科学基金会;
关键词：
FREE-RADICAL CYCLIZATIONS; DIELS-ALDER REACTIONS; UNSATURATED-KETONES; DERIVATIVES; GERANIOL; LINALOOL; ALCOHOLS; CYCLASE;
D O I：
10.1039/c0sc00284d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A stereodivergent synthesis of the [3.3.1] bicyclic core of edaxadiene was completed utilizing a key intramolecular oxidative ketone allylation. Significant discrepancies between the spectroscopic data obtained for the synthetic construct and the natural isolate raised questions about the structural assignment of edaxadiene. A subsequent structural reassignment was validated by completion of a total synthesis of the correct structure of the natural product.
引用
收藏
页码：202 / 205
页数：4
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