Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of Bridged Steroids. V. Cholestane Derivatives having a Bridged 3-Azabicyclo [3. 3. 1] nonane Ring System
WATARU NAGATATSUTOMU SUGASAWATSUTOMU AOKI
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1968 Volume 16 Issue 8 Pages 1556-1560

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Abstract
Cholestane derivative (IIb) having a bridged 3-azabicyclo [3. 3. 1] nonane ring system was synthesized from 3-oxo-5α-cholestane-5-carbonitrile (III) by a six-step reaction sequence. The over-all yield was very high indicating high stereospecificity or uniformity of the reaction used. Reduction of 3α-formyl-3β-methyl-5α-cholestane-5-carbonitrile (VIII) to the amino alcohol (Xa) was effected by means of lithium aluminum hydride reduction in the presence of aluminum chloride.
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© The Pharmaceutical Society of Japan
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