5 Allyl 9 oxobenzomorphans. IV. Synthesis of 3 hydroxy 8 oxyisomorphinans, 5 allyl 9α hydroxy 6,7 benzomorphans, and related tetrahydrofuranobenzomorphans

Article abstract of DOI:10.1139/v77-347

A series of 3-hydroxy-8-oxyisomorphinans was synthesized from the corresponding 5-allyl-9β-hydroxy-6,7-benzomorphans via a hydroboration, oxidation, mesylation and cyclization sequence of reactions. Selective reduction of and methylmagnesium iodide addition to 5-allyl-2'-methoxy-2-methyl-9-oxo-6,7-benzomorphan gave the respective 9α-hydroxy-6,7-benzomorphans. These were transformed to a number of 2-substituted-5 allyl-2',9β-dihydroxy-6,7-benzomorphans and corresponding methyltetrahydrofurano analogs.