Synthesis of cis- and trans-Davanoids: Artemone, Hydroxydavanone, Isodavanone, and Nordavanone

被引：10
|
作者：
Wan, Kanny K. [1 ]
Evans-Klock, Corwyn D. [1 ]
Fielder, Brian C. [1 ]
Vosburg, David A. [1 ]
机构：
[1] Harvey Mudd Coll, Dept Chem, Claremont, CA 91711 USA
来源：
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 11期
基金：
美国国家科学基金会;
关键词：
davanone; terpenoids; total synthesis; stereoselective synthesis; green chemistry; asymmetric allylic O-alkylation; ARTEMISIA-PALLENS; (+)-DAVANONE;
D O I：
10.1055/s-0033-1338429
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise and versatile synthesis of both cis and trans diastereomers of the natural products artemone, hydroxydavanone, isodavanone, and nordavanone has been accomplished. The preparation of trans-davanone is also described. Each synthesis is six to eight steps from geranyl acetate, with differentiation between cis and trans products occurring through a diastereoselective cyclization prior to derivatization. Many of these compounds are minor components of davana oil and have now been synthesized for the first time.
引用
收藏
页码：1541 / 1545
页数：5
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