STEREOSELECTIVE SYNTHESIS OF THE PROPOSED AMERICAN CONEFLOWER JUVENILE-HORMONE MIMIC - SOME OBSERVATIONS ON THE CYCLOPROPYLCARBINYL REARRANGEMENT IN SUBSTITUTED SYSTEMS

被引：26

作者：

COOKE, MP

机构：

[1] Department of Chemistry, Washington State University, Pullman, Washington

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 14期

关键词：

D O I：

10.1021/jo01328a027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of the proposed structure (1) of echinolone, the potent juvenile hormone mimic from the American coneflower, is reported. Oxygen and trisubstituted olefin functionality were introduced through a cyclopropylcarbinyl rearrangement of carbinol 25. The complexity of related rearrangements in model systems has been found to be a function of the presence or absence of remote unsaturation. Synthetic racemic 1 has been found to be devoid of JH activity in a standard assay, and these results are discussed with regard to the structure of the natural product. © 1979, American Chemical Society. All rights reserved.

引用

页码：2461 / 2468

页数：8