Synthesis of Sesquiterpene Anti-Tumor Lactones. IV1. A Stereoselective Synthesis oftrans-2,3-Epoxycyclohexanol
- 1 January 1976
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 6 (4) , 277-280
- https://doi.org/10.1080/00397917608063522
Abstract
In connection with studies directed toward the synthesis of sesquiterpene anti-tumor lactones, we needed the diastereomeric epoxy alcohols 1 and 2. The cis isomer 1 is obtained stereoselectively (91% 1, 9% 2) by the oxidation of 2-cyclohexen-1-o1 with m-chloroperoxy-benzoic acid.2 The only reported route to the trans isomer is a non-selective oxidation of 2-cyclohexen-1-y1 acetate with peroxybenzoic acid. After hydrolysis of the acetate, alcohols 1 and 2 are obtained in a ratio of 43:57.Keywords
This publication has 2 references indexed in Scilit:
- Epoxidation of allylic alcohols with peroxy-acids. Attempts to define transition state geometryJournal of the Chemical Society B: Physical Organic, 1970
- 376. Aspects of stereochemistry. Part I. Stereospecificity in formation of epoxides from cyclic allylic alcoholsJournal of the Chemical Society, 1957