Tetrahedron p. 2665 - 2679 (1985)
Update date:2022-08-03
Topics:
Aubert
Begue
Bonnet-Delpon
A new backbone rearrangement is observed in A/B cis methyl lithocholate derivatives. It is initiated from the C-3 carbon either by dehalogenation of the chloroesters 1 by AgSbFg6 or by the action of the triflic anhydride on the si1y1ated ether 2. This rearrangement leads to methyl diacholenate 3 and new lactones in D-homoandrostane series 5 and 6. The differences of behaviour between A/B cis and A/B trans series and the mechanism of rearrangements are discussed.
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