Thionium analogs of the opiates levorphanol and isolevorphanol: synthesis of the 17-deaza-17-thia isosteres (sulforphanol and isosulforphanol)

The total synthesis of the position-17 sulfur analogs of the perchlorate salts of the morphinans, (±)-levorphanol and (±)-isolevorphanol via4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene, a key intermediate in the synthesis of butorphanol ( 4 ), is described. 2D-Correlation and heter...

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Veröffentlicht in:	Canadian journal of chemistry 1986-01, Vol.64 (1), p.110-118
Hauptverfasser:	Belleau, B, Gulini, U, Camicioli, R, Gour-Salin, B. J, Sauvé, G
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties
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Zusammenfassung:	The total synthesis of the position-17 sulfur analogs of the perchlorate salts of the morphinans, (±)-levorphanol and (±)-isolevorphanol via4a-(2-aminoethyl)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene, a key intermediate in the synthesis of butorphanol ( 4 ), is described. 2D-Correlation and heterocorrelation nuclear magnetic resonance spectroscopy confirmed the configurational relationship of the isosteres.
ISSN:	0008-4042 1480-3291
DOI:	10.1139/v86-019