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 | Zendy

Petrović Goran B. | Zendy; Saičić Radomir N. | Zendy; Čeković Živorad M. | Zendy

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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

Author(s) -

Petrović Goran B.,

Saičić Radomir N.,

Čeković Živorad M.

Publication year - 2003

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200390258

Subject(s) - chemistry , methylene , carboxylate , ethyl acetate , olefin fiber , intramolecular force , stereochemistry , ethyl acrylate , michael reaction , medicinal chemistry , alkylation , acrylate , organic chemistry , catalysis , polymer , monomer

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 ).

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