Bioinspired Synthesis of a Sedaxane Metabolite Using Catalytic Vanadyl Acetylacetonate and Molecular Oxygen
详细信息 查看全文
- 作者：Sameer Tyagi ; Christopher D. Cook ; Dana A. DiDonato ; Jeffrey A. Key ; Bruce P. McKillican ; William J. Eberle ; Timothy J. Carlin ; David A. Hunt ; Samantha J. Marshall ; Nichola L. Bow
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：December 18, 2015
- 年：2015
- 卷：80
- 期：24
- 页码：11941-11947
- 全文大小：421K
- ISSN：1520-6904
文摘
A bioinspired synthesis of the sedaxane metabolite 2 from intermediate 3 using catalytic VO(acac)2 and O2 is described. Intermediate 3 was synthesized starting from 2-bromostyrene in four steps. The inner cyclopropyl ring of 3 was assembled with trans geometry using a highly diastereoselective Nishiyama cyclopropanation, and the outer hydroxycyclopropyl ring was installed using the Kulinkovich cyclopropanation. Additionally, conversion of 3 into 2 was demonstrated in in vitro microbial culture experiments consisting of bacteria and fungi.