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Okamoto, Y. ; Dirnberger, D. ; Burgemeister, T. ; Dannhardt, G. ; Wiegrebe, Wolfgang

Bishydrocotarnines - Stereochemical Aspects

Okamoto, Y., Dirnberger, D., Burgemeister, T., Dannhardt, G. and Wiegrebe, Wolfgang (1986) Bishydrocotarnines - Stereochemical Aspects. Archiv der Pharmazie 319, pp. 1122-1129.

Date of publication of this fulltext: 07 Jul 2010 05:03
Article
DOI to cite this document: 10.5283/epub.15662


Abstract

The bishydrocotarnines 2a and 2b1)' **) 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 ...

The bishydrocotarnines 2a and 2b1)' **) 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.

Die Bishydrocotarnine 2a und 2b1) werden in die Urethane 9a und 9b bzw. in die Carbamate 10a und 10b
umgewandelt. Spaltung von 10a bzw. 10b in die sek. Amine 11a und 11b und deren Cyclisierung führen
zu den Diketopiperazinen 12a und 12b. 9a ließ sich im Gegensatz zu 9b an einer Cellulosecarbamat-Säule
in Enantiomere spalten. Danach ist 9a die D, L-, 9b die meso-Form. NMR-Spektren von 12a und 12b führen
zu derselben Schlußfolgerung.


Involved Institutions


Details

Item typeArticle
Journal or Publication TitleArchiv der Pharmazie
Publisher:John Wiley & Sons
Volume:319
Page Range:pp. 1122-1129
Date1986
InstitutionsChemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Wiegrebe
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgUnknown
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-156629
Item ID15662

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