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A New Preparation of 1,3,3-Trimethylbicyclo[2.2.2]octan-2,6-dione, a Never Isolated Intermediate in a Total Synthesis of (+)-Norpatchoulenol. Formal Total Synthesis of (±)-Iso-Norpatchoulenol

✍ Scribed by Angela La Bella; Francesca Leonelli; Ilse De Salve; Luisa M. Migneco; Rinaldo Marini Bettolo

Book ID
102258339
Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
106 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new preparation and the isolation and spectroscopic characterization of 1,3,3‐trimethylbicyclo[2.2.2]octan‐2,6‐dione (3), a so far elusive key intermediate in the Liu–Ralitsch total synthesis of (+)‐norpatchoulenol ((+)‐1a), is described. The preparation of 3 constitutes also a formal total synthesis of (±)‐iso‐norpatchoulenol ((±)‐1b), since 3 is correlated to an intermediate in the Monti and co‐workers synthesis of (±)‐1b.

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NMR spectroscopic identification of (1S,
NMR spectroscopic identification of (1S, 4R, 6R)- and (1S, 4R, 6S)-1,3,3-trimethyl-2-oxo-6-(2-oxopropyl)bicyclo[2.2.2]octane, key intermediates towards the total synthesis of (+)-norpatchoulenol
✍ Hsing-Jang Liu; Milan Ralitsch 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 394 KB

## Abstract High‐field NMR studies of (1__S__, 4__R__, 6__R__)‐ and (1__S__, 4__R__, 6__S__)‐1,3,3‐trimethyl‐2‐oxo‐6‐(2‐oxopropyl)bicyclo[2.2.2]octane were carried out by one‐ and two‐dimensional methods. The stereochemical aspects of these molecules were studied through the application of the nucl