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

Abstract

2-Azalauren-1-ene (2) has been synthesized from keto acid (5), but attempts to generate its C15 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 hydroxy imine (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.