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•Sapogenin isomerizations catalyzed by BF 3 ·OEt 2 do not occur at C-22 but at C-25.•Sarsasapogenin acetate isomerization with BF 3 ·OEt 2 yields smilagenin acetate (not 22-epi-sarsasapogenin acetate).•Diosgenin acetate isomerization with BF 3 ·OEt 2 affords yamogenin acetate in a tiny yield.•Yamogenin treated with BF 3 ·OEt 2 yields...
(22S,23S)-23-Bromosapogenins undergo rearrangement to the (22S,23R)-22-hydroxy-23,26-epoxyfurostanes during alkaline hydrolysis. An efficient degradation procedure of sarsapogenin via the corresponding bisfuran to the C 22 lactone is described.
Five 16α,17α-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16α,17α-epoxides proved resistant to bases unless a C(22) O group was present; in the case of 22-esters or 22-ketones the oxirane rings were cleaved with base and the corresponding allylic alcohols were formed. The reactions...
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