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Sterols with Cyclopropane‐Containing Side Chains: Synthesis and Acid Isomerization
Author(s) -
Tarchini Claudio,
Rohmer Michel,
Djerassi Carl
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620431
Subject(s) - cyclopropane , chemistry , isomerization , side chain , stereochemistry , organic chemistry , ring (chemistry) , catalysis , polymer
To test the eventual involvement of sterols with a cyclopropane containing side chain in bio‐methylation processes, 24,25‐methanocholest‐5‐en‐3β‐ol ( 5 ) and 24,25‐methano‐26‐methylcholest‐5‐en‐3β‐ol ( 6 ) were synthesized. Together with the naturally occurring cyclopropane petrosterol ( 1 ), they were submitted to acid isomerization to provide chemical models for some of their potential metabolites.