Directed ortho Metalation Studies on Podocarpic Acid Derivatives: Advantageous Use of a LICKOR Base

Abstract

Methyl 13-(N,N- diethylcarbamoyl )-12-methoxypodocarpa-8,11,13-trien-19-oate (2), 13-(N,N- diethylcarbamoyl )-12,19-dimethoxypodocarpa-8,11,13-triene (8) and N,N-diethyl-2-methoxy-4,5-dimethylbenzamide (15) were prepared for studies involving lithiation directed ortho to the tertiary amide group, in which the use of a LICKOR base was advantageous. Some dynamic features of the n.m.r. spectra of the amides are discussed. Oxazoline derivatives of both tile monocyclic and diterpenoid compounds were synthesized.