๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

Synthetic analgesics: preparation of racemic 6,7-benzomorphans

โœ Scribed by Dale L. Boger; Mona Patel; Michael D. Mullican


Book ID
104219662
Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
224 KB
Volume
23
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

โœฆ Synopsis


A simple preparation of Z-carbomethoxy-Z-azabicyclo[3.3.llnonan-6-one (7_) and its conversion to the racemic benzomorphans: 2, lo, VJ are described. With a few notable exceptions, past as well as current synthetic approaches to the morphine related analgesics, including the morphinans and benzomorphans, cyclization of 2-(arylmethyl)-tetrahydrooyridines, have relied on the acid-catal.;z;d chemistry pioneered by Grewe in the 1940's ' . In addition to the limitations this places on the aryl portion of these systems, this and related synthetic approaches often lack effective stereocontrol and restrict the potential for the preparation of natural and synthetic analgesics in the desired optically pure form3. In recent communications, we have described the development and application of several different aryl annulations and in each instance a keto group served as the necessary functionality for the introduction of the aryl ring, equation 14. Eqn. (1) As the first stage in the development of new, and potentially useful, synthetic approaches to the morphine related analgesics we would like to report a simple and direct preparation of racemic 6,7-benzomorphans based on this preliminary work, equation 2 and scheme I-II.


๐Ÿ“œ SIMILAR VOLUMES


Synthesis of 6,7-benzomorphan from 4-phe
โœ Kanematsu, Ken.; Parfitt, Robert T.; Jacobson, Arthur E.; Ager, J. Harrison.; Ma ๐Ÿ“‚ Article ๐Ÿ“… 1968 ๐Ÿ› American Chemical Society ๐ŸŒ English โš– 257 KB