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Boron trifluoride catalysed rearrangement of 1,2-epoxy lupan-3-one

โœ Scribed by A.K. Ganguly; T.R. Govindachari; A. Manmade


Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
172 KB
Volume
23
Category
Article
ISSN
0040-4020

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Ihe boron triflucride catalysed rearrangements of steroidal epcxides have been widely reported (1). Recently, considerable interest has been shown in the backbone rearrangement of 4,5-and 5,6-epoxy-steroids (1). In an attempt to elucidate the mechanism of these rearrangements in more detail, we have

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The greater yield (61%) of the 6-ketone (2a) from 3a-acetoxy-5,6a-epoxy-5a-cholestane (la) compared with the yield (34%) of B-ketone (2b) from the corresponding 3-deoxy compound has been ascribed' to the energetically favourable conformational change, involving the 3-acetoxy group, in the formation