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Synthesis of New Nepenthone Derivatives
Author(s) -
Marton János,
Szabó Zoltán,
Simon Csaba,
Hosztafi Sándor,
Makleit Sándor
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619961025
Subject(s) - chemistry , phenylmagnesium bromide , alcohol , enantiomer , crystallization , derivative (finance) , organic chemistry , fractional crystallization (geology) , bromide , medicinal chemistry , reagent , geochemistry , basalt , financial economics , economics , geology
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.