title: Synthesis of ring D modified morphinan systems via ring expansion of a key codeine intermediate
abstract: Ring expansion and ring fragmentation products were synthesized from pentacyclic ketones 3 and 4 via Baeyer-Villiger oxidation. Oxidation of 3 with m-chloroperbenzoic acid afforded delta-lactone 9 which was transformed to enone 12 en route to the C6 inverted ether 14. Analogous oxidation of 4 gave delta-lactone 18. Opening of the lactone ring of 14 and 18 led to seco structures which, in the case of 19, underwent reannulation with incorporation of nitrogen to yield the hydroxylactam 21.
authors.affiliation: Department of Chemistry, Oregon State University, Corvallis 97331-4003, USA.
authors.initials: JD
authors.lastname: White
authors.initials: P
authors.lastname: Hrnciar