Synthese von Oxy‐morphinanen

Abstract

Durch die Veroffentlichungen von R. Grewel Die pharmakologische Prufung der gewonnenen Oxy-N-methylmorphinane hat zu dem interessanten Ergebnis gefuhrt, dass einzig der 3-Oxy-Verbindung, ihren Athern und Acylderivaten eine analgetische Wirkung zukommt, dass aber sowohl das 2-(oder 4)-Oxyderivat als auch aUe Zwischenprodukte der Gewinnung der beiden Oxyverbindungen als Analgetica unbrauchbar sind. Das 3-Oxy-Nmethyl-morphinan ist wesentlich wirksamer als das N-Methyll) Naturwiss. 33, 333 (1946).2, Z. angew. Ch. 59, 194 (1947).

General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-ruthenium(II) complexes

“…The formyl base, (S)-27a, directly undergoes the acid-catalyzed Grewe cyclization giving a morphinan structure which is convertible to dextromethorphan (23a), an important commercial antitussive agent. 45 In addition 27b acts as an intermediate leading to dextrophan (23b), an anticough drug.46 The levorotatory isomer, (R)-27a, can be transformed to levallorphan and oxilorphan, narcotic antagonists, as well…”

Stability of ionic liquids in Brønsted-basic media

“…150 Organolithium reagents and Grignard reagents add to the 2position in pyridinium cations in an analogous manner to yield 2-alkyl or 2-aryl-1,2dihydropyridines. [151][152][153] Nevertheless, Law et al have described the synthesis and use of Grignard reagents in pyridinium ionic liquids. 154 An additional coordinating ligand (pyridine) was required to stabilize the Grignard reagent in solution and obtain the desired Grignard reaction products.…”

The Chemopharmacological Approach to the Addiction Problem

“…Meanwhile another German chemist, work¬ ing on the synthesis of morphine, carried his work up to a morphinan structure (21), and this in turn was developed to the clinically useful product, levorphanol, by Schnider and Grussner (22). Although 3-hydroxy-N-methylmorpIu-nan (levorphanol, Dromoran) represented an incomplete morphine synthesis, it demonstrated that some features of the morphine structure could be omitted without impairment of the characteristic morj>hine effects.…”