From diplopterol to tetrahymanone: A simple chemical transformation from the hopane series to the gammacerane series

From diplopterol to tetrahymanone: A simple chemical transformation from the hopane series to the gammacerane series. Amongst all triterpenoids, the hopane and gammacerane series are closely related both from a biosynthetic as well as from a structural point of view. Substances from both classes are...

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Published inComptes rendus. Chimie Vol. 8; no. 11-12; pp. 1960 - 1968
Main Authors Maane, ZA, Bisseret, P, Llopiz, P, Neunlist, S
Format Journal Article
LanguageEnglish
French
Published ISSY-LES-MOULINEAUX Elsevier 01.11.2005
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
tetrahymanone
BACTERIA
gammacerane
triterpenoids
SEDIMENTS
hopane
SQUALENE
DIOXIDE
TRITERPENES
EPOXIDES
diplopterol
SAPONINS
RING-ENLARGEMENT
CYCLIZATION
LIPIDS
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Summary:From diplopterol to tetrahymanone: A simple chemical transformation from the hopane series to the gammacerane series. Amongst all triterpenoids, the hopane and gammacerane series are closely related both from a biosynthetic as well as from a structural point of view. Substances from both classes are used by geochemists as specific biomarkers for organisms producing them. We present here a process allowing for the first time the transformation of diplopterol of the hopane series into tetrahymanone of the gammacerane series. Each step has been optimised and the characterisation of the main secondary products has been performed.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:1631-0748
1878-1543
DOI:10.1016/j.crci.2005.06.003