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A Novel Three-Carbon Ring Expansion Sequence Synthesis of Exaltone® and (±)-Muscone

✍ Scribed by Charles Fehr

Publisher
John Wiley and Sons
Year
1983
Tongue
German
Weight
437 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Intramolecular Grignard‐type reaction of the bromo lactones 3 and 8 affords the macrocycles 10, 11, 12 and 13, 14, 15, respectively. More efficiently, 10 and 13 are obtained by intramolecular nucleophilic attack of the carbanions derived from the sulfonyl lactones 20 and 22 and in situ reduction of the intermediate sulfones 21 and 23. The macrocylic hydroxy ketones 10 and 13 are converted into Exaltone® (2) and muscone (1), respectively.

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✍ Charles Fehr 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 381 KB 👁 1 views

## Abstract Treatment of the sulfonyl ketones **1a** and **1b** with potassium __t__‐butoxide in toluene or with potassium hydroxide in toluene/dimethyl sulfoxide affords in high yield the bicyclic dienes **3a** and **3b**, important precursors for __Exaltone__® and (±)‐muscone. An application of t