Studies in the synthesis of C-ring bridged morphinans 3—13C NMR analysis of some simple and complex bicyclooctane derivatives

✍ Scribed by Victoria F. Roche; Donald L. Nagel; Edward B. Roche

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: English
• Weight: 507 KB
• Volume: 23
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1260230916

✦ Synopsis

The "C NMR spectra of eight novel derivatives of bicydo[2.2.2]-and -[3.2.l]octane have been recorded and analysed. Tbese compounds were isolated and characterized as intermediates in the synthesb of a unique derivative of 1,2,3,3a,llb,llc-hexahydroahydroaporphine. Carbon chemical shift assignments of the molecules under investigation were based on "C NMR theory induding splitting patterns, diflerences in chemical shift values of carbons a and f 3 to amino nitrogens in their protonated and non-protonated forms, and through the antiapated shielding effects of y-syn and y-anti heteroatoms. This latter method of analysis was particularly useful in assigning the chemical shift values of carbons in the bicydooctane region of the simpler molecules.

In the course of the synthesis of a unique bridged derivative of hexahydroaporphine, 3,l lc-ethano-10hydroxy-6 -methyl -1,2,3,3a, 1 lb, 1 l chexahydroaporphine (l), eight novel bicyclo[2.2.2]-and -[3.2.l]octane derivatives have been isolated and characterized spectroscopically, including analysis by 13C NMR.