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Part I. The synthesis of 6-AZA pregnane derivatives : Part II. Studies relating to alkaloid tatl synthesis

University of British Columbia

Ozonization of Ʒβ, 20β -diacetoxy-5-pregnene-7-one (XII) gave methyl Ʒβ ,20β -diacetoxy-5-oxo-5,7-seco-6-norpregnan-7-oate (XIII). Treatment of the latter with sodium hydroxide yielded methyl 20β -acetoxy-5-oxo-5,7-seco-6-nor-Ʒ-pregnen-7-oate (XIV), which upon reduction gave methyl 20β -acetoxy-5-oxo-5,7-seco-6-norpregnan-7-oate (XV) in high yield (see Figure 20). Upon treatment of the latter with benzylamine, ring closure occurred and the enol lactam, 20β -acetoxy-N-benzyl-6-aza-4-pregnen-7-one (XVI) was formed. Catalytic reduction of the double bond followed by reduction of the carbonyl with lithium aluminum hydride yielded 20β -hydroxy-N-benzyl-6-aza-5§ -pregnane (XVIII) .

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2011-10-24

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http://hdl.handle.net/2429/38204

Chemistry

University of British Columbia

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