183626-74-6Relevant articles and documents
Synthesis of scopin acetate and 6,7-didehydrohyoscyamin. Intramolecular phenylsulfenylation of a nonactivated methylene group of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate
Petrovi?, Goran B.,Sai?i?, Radomir N.,?ekovi?, ?ivorad M.
, p. 3179 - 3186 (2007/10/03)
The synthesis of scopin acetate (6b) and 6,7-didehydrohyoscyamine (17) was achieved by using tropine (5) as the starting compound. Formal (phenylthio)-radical transfer to the nonactivated 6-position of ethyl N-demethyl-3-O-(phenylthio)tropine-N-carboxylate (9) by irradiation in the presence of hexabutyldistannane is a key step of this synthetic approach, involving ethyl 6,7-didehydro-N-demethyltropine-N-carboxylate (15) as a synthetic intermediate (Schemes 3 and 5). The reaction of 9 with tributylstannane in the presence of ethyl acrylate, as a radicophilic olefin, involves Michael-type alkylation at C(6) of the tropine skeleton affording ethyl N-demethyl-N-(ethoxycarbonyl)tropine-6-propanoate (18) (Scheme 6).
Analgesic, antimuscarinic activity and enantioselectivity of the four isomers of 3-quinuclidinyl tropate as compared with the enantiomers of hyoscyamine
Dei,Bellucci,Gualtieri,Romanelli,Scapecchi,Teodori,Bartolini,Ghelardini
, p. 303 - 309 (2007/10/02)
The four stereoisomers of 3-quinuclidinyl tropate (2) were synthesized and their absolute configuration established. The analgesic activity of the four isomers on the hot-plate test and their muscarinic antagonism on rabbit vas deferens (M1), g
