1948
DOI: 10.1002/cber.19480810402
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Synthesen in der Phenanthren‐Reihe, VI. Mitteil.: Synthese des Morphinans

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Cited by 104 publications
(24 citation statements)
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“…The little known pharmacological profiles of the (+)-enantiomers of 6-keto-morphinans suggested that a total synthesis of 12a be conceived, which would allow at the same time the preparation of its optical isomer 12b. The Grewe cyclization of appropriately substituted octahydroisoquinolines, chosen as the key reaction in the synthesis of 12a, b, is greatly facilitated by the presence of an electron withdrawing group on the amine nitrogen (4), and a hydroxy group para-positioned at the point of ring closure (5). It seemed therefore advisable to first attempt the synthesis of 2-hydroxy substituted 6-ketomorphinans, also needed for our SAR studies, and to eliminate the phenolic 2-hydroxy group afterwards.…”
mentioning
confidence: 99%
“…The little known pharmacological profiles of the (+)-enantiomers of 6-keto-morphinans suggested that a total synthesis of 12a be conceived, which would allow at the same time the preparation of its optical isomer 12b. The Grewe cyclization of appropriately substituted octahydroisoquinolines, chosen as the key reaction in the synthesis of 12a, b, is greatly facilitated by the presence of an electron withdrawing group on the amine nitrogen (4), and a hydroxy group para-positioned at the point of ring closure (5). It seemed therefore advisable to first attempt the synthesis of 2-hydroxy substituted 6-ketomorphinans, also needed for our SAR studies, and to eliminate the phenolic 2-hydroxy group afterwards.…”
mentioning
confidence: 99%
“…It is known that metal halides are not active in so-called Lewis acid catalyzed reactions of olefins in the To demonstrate the viability of the N-formyloctahydroabsence of a co-catalyst [25] . Therefore, an explanation for isoquinolines as starting compounds for the synthesis of Nthe activation of the enamide double bond in the presence formylmorphinans we applied the acid-catalyzed cyclization of a Lewis acid might be protonation by a superacid which of the octahydroisoquinolines to the morphinan skeleton, is formed when trace amounts of water or triflic acid are known as the Grewe cyclization [27] . We found that for these present in the reaction mixture.…”
Section: Synthesis Of Morphinansmentioning
confidence: 99%
“…N-Methylmorphinan (40) was synthesized in 1946 (58,59). The 3-hydroxyl and the 3-methoxy analogues were prepared by the same method.…”
Section: Nonnarcotic Antitussivesmentioning
confidence: 99%