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Title

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

Authors
Schüpfer, Patrick
Houot, Frédéric
Published in Organic Geochemistry. 2007, vol. 38, no. 4, p. 671-681
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.
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Research group Groupe Gülaçar
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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. https://archive-ouverte.unige.ch/unige:3587

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Deposited on : 2009-10-02

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