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Synthetic studies in steroidal sapogenins and alkaloids—XII : Synthesis of sceptrumgenin and isonuatigenin
Authors:S.V. Kessar  Manohar Lal  R.K. Mehra  Y.P. Gupta
Affiliation:Department of Chemistry, Panjab University, Chandigarh, India
Abstract:The Michael adduct of 5-nitro-2,2-ethylene-dioxypentan-1-ol acetate with E-5,17(20)-pregnadien-3β-ol-16-one gave on reduction with sodium borohydride and deketalisation, spirost-5-en-3β-ol-25-one. This intermediate was converted to sceptrumgenin through reaction with triphenyl phosphonium methylide and to isonuatigenin by treatment with dimethyl oxosulfonium methylide followed by lithium aluminium hydride.
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