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Biomimetic total synthesis of steroids IV. Stereoselective synthesis of 15α-methyl-19-norsteroids

✍ Scribed by M.B. Groen; F.J. Zeelen

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
406 KB
Volume
98
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The cationic cyclization of 2‐[6‐(m‐methoxyphenyl)‐(E)‐3‐hexenyl]‐3,5‐dimethyl‐2‐cyclopentenol (3) was investigated. Exclusive formation of 1‐ and 3‐methoxy‐15α,17‐dimethyl‐1,3,5(10), 13(17)‐gonatetraene (4 and 5) was observed, indicating complete stereoselectivity in the cyclization process. Compound 4 was converted into dl‐15α‐methylestrone methyl ether (7) and hence into dl‐15α‐methylestradiol 3‐methyl ether (8). The structure of these hitherto unknown compounds was proved by independent syntheses.

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Biomimetic total synthesis of steroids V
Biomimetic total synthesis of steroids VI. Stereospecific synthesis of 19-nor-8α-steroids and 11α-alkyl derivatives
✍ M. B. Groen; B. Hindriksen; F. J. Zeelen 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 721 KB

## 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 appro