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Synthesis of New Nepenthone Derivatives

✍ Scribed by Marton, János ;Szabó, Zoltán ;Simon, Csaba ;Hosztafi, Sándor ;Makleit, Sándor

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
402 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Hydrogenation of nepenthone (3a) leads to a mixture of dihydronepenthone (3c) and the secondary alcohol (20__S__)‐4b. The enantiomeric secondary alcohol (20__S__)‐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 (20__S__)‐4b and (20__R__)‐4b, which are separated by fractional crystallization. The conformations of (20__S__)‐4b and (20__R__)‐4b are determined by NOE difference experiments.

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