Complete H-1 and C-13 chemical shifts assignments for 12 octahydroisoquinol
ine derivatives, intermediates in the synthesis of morphine, were made base
d on 2D NMR spectroscopy. The stereochemistry of the compounds characterize
d by the decahydroisoquinoline skeleton was elucidated based on the value o
f the H-1-H-1 vicinal coupling constants, which were measured in the phase-
sensitive DQCOSY spectrum. An approach based on the pattern of the relative
intensity of the cross peaks in the NOESY spectrum was taken to determine
the stereochemistry of the epoxides derived from octahydroisoquinoline. A p
attern of coupling constants was identified in each of the series, allowing
the assignment of the epoxide relative stereochemistry by means of the pro
ton spectrum only. For each type of stereochemistry, x-ray data of represen
tative compounds confirmed the configuration determined by NMR. Copyright (
C) 1999 John Wiley & Sons, Ltd.