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Probes for Narcotic Receptor Mediated Phenomena : Synthesis of rac-(3R,6aS,11aR)-1,3,4,5,6,11a-Hexahydro-2-methyl-2H-3,6a-methanobenzofuro[2,3-c]azocin-8-ol, an Epoxy Isomer of 5-Phenylmorphan

✍ Scribed by Joannes T. M. Linders; Seid Mirsadeghi; Judith L. Flippen-Anderson; Clifford George; Arthur E. Jacobson; Kenner C. Rice

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
162 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of a series of epoxy 5‐phenylmorphans is being explored in order to determine the conformational requirements of the phenolic ring in a phenylmorphan molecule that may be needed both for binding to a specific opioid receptor and for exhibiting opioid agonist or antagonist activity. Of the twelve possible ortho‐ and para‐bridged isomers (a–f) (Fig. 1), we now report the synthesis of the para‐d isomer, rac‐(3__R__,6a__S__,11a__R__)‐2‐methyl‐1,3,4,5,6,11a‐hexahydro‐2__H__‐3,6a‐methanobenzofuro[2,3‐c]azocin‐8‐ol (3). Compound 3 was synthesized via construction of the 5‐phenylazabicyclo[3.3.1]non‐3‐ene skeleton (Scheme 1) and subsequent closure of the epoxy bridge (Scheme 2). As determined by an X‐ray diffraction study, the epoxy bridge, restricting the phenyl‐ring rotation, fixed the dihedral angle between the least‐squares planes through the phenyl ring and atoms N(2), C(3), C(11a), and C(6a) of the piperidine ring (Fig. 2) at 43.0°, and the torsion angle C(12)C(6a)C(6b)C(10a) at −95.0°.

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