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Attempted Skeletal Rearrangements in the Lanostane Series
Author(s) -
Levy E. C.,
Lavie D.
Publication year - 1970
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.197000082
Subject(s) - lanostane , chemistry , ring (chemistry) , hydrolysis , stereochemistry , derivative (finance) , organic chemistry , triterpene , medicine , alternative medicine , pathology , financial economics , economics
The conversion of a lanostane skeleton into a cucurbitane (C‐9β‐Me) has been explored. Several derivatives with an oxirane ring in the appropriate location to induce a methyl migration (while having an adjacent oxygen function as required in the cucurbitacins) have been treated with SnCl 4 . The reaction took however, a different course and the products have been analysed and identified. During treatment with SnCl 4 of the epoxy‐lanostane derivative having a diosphenol system in ring A, an acid stable organo‐tin complex was observed to be formed. Base hydrolysis of this complex produced compounds similar to those obtained in the previous examples.