Abstract
Lithium aluminum hydride reduction of 3β-hydroxy-11-aza-5α, 22β-spirost-8(9)-en-12-one (I) provides the enamine, II, which upon subsequent conversion to its iminium salt, IV, and borohydride reduction yields 11-aza-5α, 8ξ, 9α, 22β-spirostan-3β-ol (v). This reaction furnishes a convenient sequence for reduction of the 8, 9-double bond in 11-aza steroid derivatives. Degradation of the sapogenin side chain then allows entry into 11-aza pregnane derivatives. The synthetic sequence provides the first examples of 11-aza steroid analogues in which ring C is six-membered and completely saturated.
Published Version
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