Synthesis of Bridged Steroids. V. Cholestane Derivatives having a Bridged 3-Azabicyclo [3. 3. 1] nonane Ring System

Synthesis of Bridged Steroids. V. Cholestane Derivatives having a Bridged 3-Azabicyclo [3. 3. 1] nonane Ring System

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...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1968/08/25, Vol.16(8), pp.1556-1560
Hauptverfasser: NAGATA, WATARU, SUGASAWA, TSUTOMU, AOKI, TSUTOMU
Format: Artikel
Sprache:eng
Schlagworte:
Amino Alcohols - chemical synthesis
Bridged-Ring Compounds
Chemical Phenomena
Chemistry
Cholestanes
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.16.1556