首页 | 本学科首页   官方微博 | 高级检索  
     


Synthesis of the hydroazulene portion of guanacastepene A using a [2.3]sigmatropic sulfoxide rearrangement: observations on silyl enol ether electrophilic chemistry for the introduction of the C-13 hydroxyl group
Authors:Philip Magnus  Cyril Ollivier
Affiliation:

aDepartment of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA

Abstract:The intermediate 6 can be converted into enone 13 using a [2.3]sigmatropic sulfoxide rearrangement as the key transformation. The C-13 hydroxylation of 13 was studied, and found to give 14 (epimeric to guanacastepene A). Examination of silyl enol ethers of 13 demonstrated the ready isomerization of the kinetic silyl enol ether into the more stable thermodynamic silyl enol ether under mild electrophilic reaction conditions.
Keywords:guanacastepene   [2.3]sigmatropic rearrangement   silyl enol ethers
本文献已被 ScienceDirect 等数据库收录!
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号