Synthetic analgesics: preparation of racemic 6,7-benzomorphans
โ 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
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โฆ 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.
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