Concise synthesis of Cannabisin G

Dawei Li; Wenling Li; Qian Wang; Zhaoqi Yang; Zijie Hou

doi:10.1016/j.bmcl.2010.07.028

Concise synthesis of Cannabisin G

Bioorg Med Chem Lett. 2010 Sep 1;20(17):5095-8. doi: 10.1016/j.bmcl.2010.07.028. Epub 2010 Jul 11.

Authors

Dawei Li¹, Wenling Li, Qian Wang, Zhaoqi Yang, Zijie Hou

Affiliation

¹ Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, PR China.

PMID: 20667725
DOI: 10.1016/j.bmcl.2010.07.028

Abstract

Cannabisin G (1), a naturally occurring lignanamide, was synthesized in 45% overall yield starting from 3-tert-butyl ethyl ferulate (6). An oxidative coupling by potassium ferricyanide in an alkaline media serves as the key step to construct the biphenylbutadiene skeleton of 1 with high regioselectivity.

MeSH terms

Ferrocyanides / chemistry
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Phenols / chemical synthesis*
Spectrometry, Mass, Electrospray Ionization

Substances

Ferrocyanides
Phenols
cannabisin G
potassium ferrocyanide