Synthesis of guaipyridine and some related sesquiterpene alkaloids

Abstract Syntheses are described of guaipyridine ( 8 ) from guaiol ( 3 ) and of epiguaipyridine ( 2 ) from α‐gurjunene ( 10 ). The alkaloid isolated from Pogostemon patchouli Pellet, possesses structure 8 of guaipyridine. The configuration at C(10) was confirmed by proton magnetic resonance studies on the conformationally rigid tricyclic structures 14 and 15 . Natural α‐gurjunene was shown to be a mixture of the C(10)‐epimers 10 and 11 .