Steroid Series. XI. Synthesis of B-Norsteroid

Cholesterol acetate (Ia), 3β-hydroxypregn-5-en-20-one acetate (Ib) and 3β-hydroxyandrost-5-en-17-one acetate (Ic) were ozonized in dichloromethane containing a small amount of methanol to give the corresponding 3β-acetoxy-5-hydroxy-6-methoxy-5, 6-peroxy-5, 6-seco steroid compounds (IIa, b, c), which...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 11; no. 4; pp. 536 - 538
Main Authors Tanabe, Katsumi, Morisawa, Yasuhiro
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 1963
Japan Science and Technology Agency
Subjects
Norsteroids
Old Medline
Steroids
STEROIDS
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Summary:Cholesterol acetate (Ia), 3β-hydroxypregn-5-en-20-one acetate (Ib) and 3β-hydroxyandrost-5-en-17-one acetate (Ic) were ozonized in dichloromethane containing a small amount of methanol to give the corresponding 3β-acetoxy-5-hydroxy-6-methoxy-5, 6-peroxy-5, 6-seco steroid compounds (IIa, b, c), which on reduction with zinc dust and acetic acid afforded 3β-acetoxy-5-oxo-5, 6-secosteroid-6-als (IIIa, b, c). Cyclization reaction of (IIIa, b, c) was conducted by stirring with alumina in benzene solution to yield 6β-formyl-B-nor-5β-cholestane-3β, 5-diol 3-acetate (IVa), 6β-formyl-3β, 5-dihydroxy-B-nor-5β-pregnan-20-one 3-acetate (IVb) and 6β-formyl-3β, 5-dihydroxy-B-nor-5β-androstan-17-one 3-acetate (IVc), respectively.
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.11.536