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Morphine Alkaloids, CXVII : Investigation of the Azidolysis of Tertiary Alcohols of Thebaine Derivatives with Bridged Ring C
Author(s) -
Sepsi Ágnes,
Berényi Sándor,
Makleit Sándor,
Tóth Zoltán
Publication year - 1993
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.19933260602
Subject(s) - thebaine , chemistry , diastereomer , ring (chemistry) , stereochemistry , chirality (physics) , steric effects , stereospecificity , decalin , morphine , medicinal chemistry , organic chemistry , catalysis , medicine , nambu–jona lasinio model , chiral symmetry breaking , codeine , physics , quantum mechanics , pharmacology , quark
Replacement of the C‐19 tertiary hydroxyl group of some thebaine and oripavine derivatives with bridged ring C (so‐called Bentley 's compounds) for an azido group has been performed with hydrazoic acid. In case the hydroxyl group was connected to a centre of chirality, substitution resulted in the formation of diastereomeric mixture of azides and elimination took place as well, the extent of which was dependent mainly on steric factors. Configuration of the C‐19 has been determined by 1 H‐NMR spectra and calculated proton‐proton distances of amines 13a and 13b obtained by the reduction of 10c followed by separation.