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NMR spectroscopic identification 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, key intermediates towards the total synthesis of (+)‐norpatchoulenol
Author(s) -
Liu HsingJang,
Ralitsch Milan
Publication year - 1990
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260280307
Subject(s) - chemistry , homonuclear molecule , heteronuclear molecule , octane , coupling constant , nuclear overhauser effect , stereochemistry , nuclear magnetic resonance spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , molecule , physics , organic chemistry , particle physics
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.