ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of new eburnamine-type alkaloid via direct hydroalkoxylation

Xiong Liu, Dong-Liang Yang, Jia-Jia Liu, Jing Zhou, and Nana Zhao

Department of Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China

E-mail: liujj0903@163.net

Abstract: This study concerns the preparation of a new eburnamine-type alkaloid, methyl (3α,14β,15β,16α)-17,18-didehydro-14,15-dihydroeburnamine-15-methoxy-14-carboxylate (VIII). This alkaloid was prepared from (+)-17,18-dehydroapovincamine (V) using Lewis acid and/or ion exchange resin as catalyst. The hydroalkoxylation reaction of V with methanol was investigated in terms of catalyst, solvent, temperature, and time of reaction. A one-pot method for synthetising this alkaloid was established. The optimal conditions for the reaction are discussed.

Keywords: eburnamine-type alkaloid – catalyst – hydroalkoxylation

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0512-8

Chemical Papers 68 (6) 816–822 (2014)