494199-22-3Relevant academic research and scientific papers
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
Linders, Joannes T. M.,Mirsadeghi, Seid,Flippen-Anderson, Judith L.,George, Clifford,Jacobson, Arthur E.,Rice, Kenner C.
, p. 484 - 493 (2007/10/03)
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 exhibiti
Probes for narcotic receptor mediated phenomena; 29: (see abstract)
Yamada, Koichiro,Flippen-Anderson, Judith L.,Jacobson, Arthur E.,Rice, Kenner C.
, p. 2359 - 2364 (2007/10/03)
A six-step synthesis of the para-a oxide-bridged phenylmorphan isomer rac-(4R,6aR,11bR)-3-methyl-2,3,4,5,6,6a-hexahydro-1H-4,11b-methanobenzofuro [3,2-d]azocin-10-ol (4), was achieved using Okahara's reagent, 3-chloro-2-methoxymethoxypropene, to prepare the key intermediate 8. Bromination was directed at the desired carbon atom via the correctly positioned ketone moiety in 8. O-Demethylation followed by subsequent displacement of the bromine by the phenolic ion in situ gave ketone 9 that, after reduction to the alcohol and conversion to the bis-mesylate, could be reduced to obtain the desired product. The structure of 4 was unequivocally determined by an X-ray spectroscopic study. A similar sequence of reactions provided a novel, much shorter synthetic route to the known ortho-a oxide-bridged phenylmorphan isomer.
