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Synthesis 2010(11): 1766-1770  
DOI: 10.1055/s-0029-1218732
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of (-)-Δ8-trans-Tetrahydrocannabinol

Qinggang Huanga, Bin Maa, Xi’an Lia, Xinfu Pana, Xuegong She*a,b
a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: shexg@lzu.edu.cn;
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Publication History

Received 21 January 2010
Publication Date:
12 April 2010 (online)

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Abstract

(-)-Δ8-trans-Tetrahydrocannabinol was synthesized with high regio- and stereoselectivity through SN2′ addition of an arylcyanocuprate to the optically pure enol silyl ether of α,β-epoxycyclohexanone.

Key words

addition reactions - heterocycles - tetrahydrocannabinol - deoxygenation - stereoselective synthesis

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