Premium
21,21,21‐Trifluorothevinone: the Straightest Way to Fluorinated Thevinols and Orvinols
Author(s) -
Sandulenko Irina V.,
Kovaleva Ekaterina S.,
Peregudov Alexandr S.,
Kalinin Valery N.,
Moiseev Sergey K.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600233
Subject(s) - thebaine , swern oxidation , adduct , chemistry , combinatorial chemistry , receptor , stereochemistry , organic chemistry , pharmacology , morphine , medicine , biochemistry , codeine , dimethyl sulfoxide
Thevinone is the key starting material for preparations of thevinols and orvinols, the well‐known opioid receptor ligands. Some of them have found applications both in human medicine and veterinary. Herein we disclose the convenient multigram‐scale preparation of 21,21,21‐trifluorothevinone that opens the straightest way to the relative C(21)‐fluorinated thevinols and orvinols, the putative opiod receptor ligands as well as the valuable objects for investigations of the structure‐activity relationship in the thevinol/orvinol series. 21,21,21‐Trifluorothevinone was prepared by a reaction of the thebaine‐based [4+2]‐adduct of acroleine with CF 3 SiMe 3 followed by the Swern oxidation of the fluorinated alcohol thus obtained.