UBC Theses and Dissertations
The synthesis of 11-aza pregnane derivatives Sood, Rattan Sagar
The Beckmann rearrangement of the oxime of 11-oxo-⍺, 20-dihydroxy-C-nor pregnane (54) provided the corresponding lactam (56). Oxidation of the latter with Jones reagent furnished the 3-keto-alcohol (57), which upon its conversion to the acetate derivative (58) followed by bromination and dehydrobromination yielded ll-aza-20-acetoxy-pregn-4-ene-3,12-dione (60). Hydrolysis of the latter to the ∆⁴ -3-keto alcohol (62) followed by oxidation furnished the desired ll-aza-pregn-4-ene-3,12,20-trione (63). The synthetic sequence provides the first examples of ll-aza steroid analogues in which ring C is a six membered and ring A possesses the ∆⁴-3-keto moiety.
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