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Structure and Properties of Cholest‐4α‐methyl‐8‐en‐3β,7α‐diol Diacetate
Author(s) -
XiuMin Shen,
YuMei Liu,
Lan He
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200590305
Subject(s) - chemistry , chloroform , diol , stereochemistry , carbon 13 nmr , organic chemistry , absolute configuration , proton nmr , selenium , medicinal chemistry
Lophenol, cholest‐4α‐methyl‐7‐en‐3β‐ol ( 1 ), obtained from Dracaena cochinchinensis (Lour.) S. C. Chen, was structurally modified. It was acetylated to protect 3β‐hydroxyl group, and then oxidised by selenium dioxide in ace‐tic acid to give cholest‐4α‐methyl‐8‐en‐3β,7α‐diol diacetate ( 3 ). This compound 3 is unstable in chloroform solution or when heated and easily converted to a diene compound, cholest‐4α‐methyl‐7,14‐dien‐3β‐ol acetate ( 4 ). The structures of 3 and 4 were elucidated by means of IR, 1 H NMR, 13 C NMR and MS, and the absolute configuration of 3 was established by X‐ray crystallography. The property of 3 was also discussed in this paper. Both 3 and 4 are new compounds and were reported for the first time.