Synthesis of ent-Kaurane and Beyerane Diterpenoids by Controlled Fragmentations of Overbred Intermediates

被引：106

作者：

Cherney, Emily C. ^{[1
]}

Green, Jason C. ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 34期

关键词：

beyerane; diterpenes; ent-kaurane; overbred intermediates; total synthesis; FREE-RADICAL CYCLIZATION; C-H BONDS; POLYENE CYCLIZATION; METHYL-GROUPS; ACID; STEREOCHEMISTRY; STEVIOL; FUNCTIONALIZATION; CYCLOPALLADATION; PHOTOADDITION;

D O I：

10.1002/anie.201304609

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Efficient access to minimally oxidized members of the ent-kaurane and beyerane class of terpenes has been achieved by using a polyene cyclization precursor designed to directly yield oxidation at the axial C19-methyl group. Construction of the [3.2.1]bicyclic system found in the ent-kaurane skeleton was realized with two overbred intermediates. Wagner-Meerwein rearrangement of the [3.2.1]bicyclic system yields the beyerane skeleton of isosteviol. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9019 / 9022

页数：4

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