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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

✍ Scribed by Hsing-Jang Liu; Milan Ralitsch

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 394 KB
Volume: 28
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260280307

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✦ Synopsis

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 nuclear Overhauser effect and stereospecific coupling constants. Unambiguous ^1^H and ^13^C chemical shift assignments have been made on the basis of two‐dimensional homonuclear (^1^H–^1^H) and heteronuclear (^1^H–^13^C) correlation spectroscopy, APT, INAPT and broad‐band proton decoupling experiments.

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