en
Scientific article
English

Acid-catalysed backbone rearrangement of cholesta-6,8(14)-diene

Published inHelvetica chimica acta, vol. 79, no. 4, p. 989-998
Publication date1996
Abstract

Rearrangement of 5- and 5-cholesta-6,8(14)-dienes (13a and 13b, resp.) in the presence of anhydrous toluene-4-sulfonic acid in acetic acid leads to 5- and 5-12(13 14)-abeo-cholesta-8,13(17)-dienes (15a and 15b, resp.) via 5- and 5-cholesta-8,14-dienes (14a and 14b, resp.), respectively. Epimerization at C(20) of the spirosteradienes 15a and 15b occurs with increasing reaction time. Molecular-mechanics calculation of the relative stabilities of these compounds and of congeners thereof is in agreement with the observed reaction pathway.

Research group
Funding
  • Swiss National Science Foundation - 20-39410.93
Citation (ISO format)
RONG-MING, Liu et al. Acid-catalysed backbone rearrangement of cholesta-6,8(14)-diene. In: Helvetica chimica acta, 1996, vol. 79, n° 4, p. 989–998. doi: 10.1002/hlca.19960790407
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0018-019X
576views
0downloads

Technical informations

Creation09/21/2009 4:03:50 PM
First validation09/21/2009 4:03:50 PM
Update time03/14/2023 3:12:08 PM
Status update03/14/2023 3:12:08 PM
Last indexation01/15/2024 6:49:19 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack