Acid-catalysed rearrangements of steroid alkenes. Part 2. A re-investigation of the backbone rearrangement of cholest-5-ene
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1071-1075
- https://doi.org/10.1039/p19880001071
Abstract
Backbone rearrangement of cholest-5-ene (1) with boron trifluoride–diethyl ether gives, in addition to the well known diacholest-13(17)-enes (4a,b), their 10β counterparts (6a,b) as minor products. With anhydrous toluene-p-sulphonic acid–acetic acid, additional products include components also isomeric at C-10 and C-20 and having a spiro C/D ring junction. A proposed scheme for the rearrangement is given.This publication has 1 reference indexed in Scilit:
- Isomerisation, rearrangement and aromatisation of steroids in distinguishing early stages of diagenesisOrganic Geochemistry, 1984