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Bishydrocotarnines – Stereochemical Aspects
Author(s) -
Okamoto Yoshio,
Dirnberger Doris,
Burgemeister Thomas,
Dannhardt Gerd,
Wiegrebe Wolfgang
Publication year - 1986
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19863191212
Subject(s) - diketopiperazines , yield (engineering) , chemistry , enantiomer , carbamate , cellulose , oxalate , column chromatography , stereochemistry , organic chemistry , materials science , metallurgy
The bishydrocotarnines 2a and 2b were converted into the urethanes 9a and 9b and into the carbamates 10a and 10b , which in turn were split to yield the sec. amines 11a and 11b . Cyclisation with diethyl oxalate led to the diketopiperazines 12a and 12b . Contrary to 9b , compound 9a was resolved into enantiomers on a cellulose carbamate column. This indicates that 9a is the D,L‐ and 9b is the meso form. NMR spectra of 12a and 12b led to an analogous conclusion.