Synthesis of dl-Meroquinene

Abstract

Meroquinene (1), a key degradation product of quinine and an important intermediate in the preparation of the cinchona and other alkaloids,¹ has only recently been synthesized ² even though attempts were made at its preparation for over thirty years. These early attempts were frustrated primarily by the difficulty encountered in the introduction of a potential vinyl group onto a piperidine ring. Alkylation of 3-car-bethoxy-N-benzoyl-4-piperidone (2) with either phenoxyethyl chloride³ or dimethylaminoethyl chloride (3)⁴ resulted in exclusive formation of the O-alkylated product, even though alkylation of the presumably analogous 2-carbethoxycyclohexanone with 3 gave nearly equal amounts of C- and O- alkylated materials.⁴ The use of other piperidone derivatives in this reaction was precluded by the report that attempts to alkylate 3-car-bethoxy-N-alkyl-4-piperidones gave only the quaternary nitrogen product.⁵