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Biomimetic total synthesis of steroids VI. Stereospecific synthesis of 19-nor-8α-steroids and 11α-alkyl derivatives

✍ Scribed by M. B. Groen; B. Hindriksen; F. J. Zeelen

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
721 KB
Volume
101
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Cationic cyclization of 2‐[6‐(3‐methoxyphenyl)‐(Z)‐3‐hexenyl]‐3‐methyl‐2‐cyclopentenol (7a) produced 1‐ and 3‐methoxy‐17‐methyl‐8α‐gona‐1,3,5(10),13(17)‐tetraene (8a and 9a) with complete stereospecificity. Cyclization of similar substrates with an alkyl substituent in the appropriate position gave exclusively 11α‐alkyl derivatives of 8a and 9a. The products were converted into the corresponding 13α,17α‐epoxides by peracid oxidation and hence into derivatives of 8α‐estrone and 8α‐estradiol. 11α‐Methyl‐8α‐estra‐1,3,5(10)‐triene‐3,17(3‐diol (16b) was obtained in its two enantiomeric forms via resolution of its 3‐methyl ether.

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