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

页码：1541 / 1545

页数：5