Diterpene Imines. The Preparation of 2-Azalauren-1-ene and the Facile Autoxidation of 6-Azadihydrorimuene

Article abstract of DOI:10.1071/CH9900719

2-Azalauren-1-ene (2) has been synthesized from keto acid (5), but attempts to generate its C 15 epimer (19) have produced only (2).Model studies of imine production by treatment of a rimuene-derived keto acid (3) with iodosylbenzene/formic acid have produced a hydroxyimine (11), a conjugated imine (13), and a keto lactam (12) which has a ten-membered ring.An X-ray crystallographic study which proves the structure of (12) is described.Data in support of the intermediacy of imine (7) (6-azadihydrorimuene) in the production of (11), (12) and (13) have been obtained.