Diastereoselective one-pot synthesis of 7- and 8-substituted 5-phenylmorphans |
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Authors: | Lim Hwan Jung Deschamps Jeffrey R Jacobson Arthur E Rice Kenner C |
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Affiliation: | Drug Design and Synthesis Section, CBRB, 5625 Fishers Lane, Room 4N03, National Institute on Drug Abuse, National Institutes of Health, DHHS, Rockville, Maryland 20852, USA. |
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Abstract: | Novel 7- and 8-alkyl and aryl substituted 5-phenylmorphans were synthesized from substituted allyl halides and N-benzyl-4-aryl-1,2,3,6-tetrahydropyridine by a highly efficient and diastereoselective reaction series, "one-pot" alkylation and ene-imine cyclization followed by sodium borohydride reduction. Mild cyclization conditions gave the desired substituted 5-phenylmorphans in good yield as a single diastereomer. |
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