ISSN:
0947-3440
Keywords:
Alkaloids
;
Morphinans
;
Dihydronepenthone
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Hydrogenation of nepenthone (3a) leads to a mixture of dihydronepenthone (3c) and the secondary alcohol (20S)-4b. The enantiomeric secondary alcohol (20S)-4b is prepared from the 7α-formyl-6,14-ethenomorphinan derivative 3b by reaction with phenylmagnesium bromide to afford a mixture of the diastereoisomeric alcohols 4a. Hydrogenation of 4a leads to (20S)-4b and (20R)-4b, which are separated by fractional crystallization. The conformations of (20S)-4b and (20R)-4b are determined by NOE difference experiments.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961025
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