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

Total synthesis of cannabisin F

Ya-Mu Xia, Jun Xia, and Chen Chai

College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

E-mail: xiaym@qust.edu.cn

Abstract: A practical eight-step synthesis of lignanamide cannabisin F starting from vanillin is reported for the first time. This synthetic strategy applies the aldol reaction followed by the Wittig reaction to afford the key 8-O-4′-neolignan intermediate diacid. The diacid was condensed with N,O-protected tyramine giving, after deprotection, cannabisin F.

Keywords: cannabisin F – lignanamide – 8-O-4′-neolignan – tyramine

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0449-y

Chemical Papers 68 (3) 384–391 (2014)