Acid catalysed backbone rearrangement of cholesta-2,4,6-triene: On the origin of ring A and ring B aromatic steroids in recent sediments

Schüpfer, Patrick; Finck, Yvan; Houot, Frédéric; Gulacar, Fazil

doi:10.1016/j.orggeochem.2006.11.004

Scientific article

English

Acid catalysed backbone rearrangement of cholesta-2,4,6-triene: On the origin of ring A and ring B aromatic steroids in recent sediments

ContributorsSchüpfer, Patrick; Finck, Yvan; Houot, Frédéric; Gulacar, Fazil

Published inOrganic geochemistry, vol. 38, no. 4, p. 671-681

Publication date2007

Abstract

Rearrangement of cholesta-2,4,6-triene in the presence of p-toluenesulfonic acid in acetic acid at 70° C leads to 4-methyl-19-nor-cholesta-1,3,5(10)-triene and 1(10 !6)-abeo-14b-cholesta-5,7,9(10)-triene in less than 2 h. Postulated mechanisms of formation of these products are supported by molecular mechanics calculations of the relative stabilities of reaction intermediates. The results suggest that D5,7-sterols, the most common natural precursors of triunsaturated steroidal hydrocarbons in contemporary sediments, constitute another major source for monoaromatic A and B steroids in addition to D5-sterols.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie physique

Research groups

Groupe Gülaçar

Citation (ISO format)

SCHÜPFER, Patrick et al. Acid catalysed backbone rearrangement of cholesta-2,4,6-triene: On the origin of ring A and ring B aromatic steroids in recent sediments. In: Organic geochemistry, 2007, vol. 38, n° 4, p. 671–681. doi: 10.1016/j.orggeochem.2006.11.004

Article (Published version)

Identifiers

PID : unige:3587
DOI : 10.1016/j.orggeochem.2006.11.004

Additional URL for this publicationhttp://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6V7P-4N2D618-1-F&_cdi=5848&_user=779890&_orig=browse&_coverDate=04%2F30%2F2007&_sk=999619995&view=c&wchp=dGLbVzz-zSkzk&md5=f6e7e85fa76d21e9909554b6029903f4&ie=/sdarticle.pdf

Journal ISSN0146-6380

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Acid catalysed backbone rearrangement of cholesta-2,4,6-triene: On the origin of ring A and ring B aromatic steroids in recent sediments

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