𝔖 Bobbio Scriptorium
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Steroid Total Synthesis, Part III. 9β, 10α-Testosterone

✍ Scribed by G. Saucy; R. Borer

Book ID
102858592
Publisher
John Wiley and Sons
Year
1971
Tongue
German
Weight
796 KB
Volume
54
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The total synthesis of 9β, 10α‐testosterone via a BCD‐tricyclic intermediate is described. The latter compound – 17β‐hydroxy‐des‐A‐androst‐9‐en‐5‐one – was obtained in optically active form by our previously reported scheme, using an efficient resolution step early in the synthesis. New results regarding the asymmetric induction step are also discussed.

📜 SIMILAR VOLUMES

Steroid Total Synthesis, Part II; (−)-17
Steroid Total Synthesis, Part II; (−)-17β-Hydroxy-des-A-androst-9-en-5-one
✍ G. Saucy; R. Borer 📂 Article 📅 1971 🏛 John Wiley and Sons 🌐 German ⚖ 848 KB

Based on the results obtained in the raceniic series (part I ) , ( -)-17P-hydroxy-des-A-androst-9-en-5-one has been synthesized, starting with (S)-( -)-5-heptanolide. The key step, viz. the condensation of ( S ) -( -)-7-hydroxy-l-nonen-3-one (or its amine adduct) with 2-methyl-cycIopentane-l,3-dione