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Enantioselective approach to morphinans

✍ Scribed by Hamid Sdassi; Gilbert Revial; Michel Pfau; Jean d'Angelo

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 253 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94652-5

No coin nor oath required. For personal study only.

✦ Synopsis

Enantioselective synthesis of morphinan derivative 2Qfrom 2,7-dimethoxynaphthalene has been achieved in twelve steps (11 % overall yield).

The morphine-like tetracyclic derivatives morphinans are widely used pharmaceutical agents'. The development of efficient enantioselective approaches to these alkaloids is essential since, in general, their chemotherapeutic properties strongly depend on their absolute co~gurations 2. Thus, for example, levorphanol 1 is a powerful analgesic (aboutfive rimes as active as morphine in humans, both on parenteral and oral 3 administrations) while dextrorphan 2, which possesses the opposite absolute configuration, is a cough suppressant drug 4, free from the undesirable opiate psychomimetic side-effects t.

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