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

Qinggang Huang; Bin Ma; Xi’an Li; Xinfu Pan; Xuegong She

doi:10.1055/s-0029-1218732

PAPER

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

Qinggang Huang^a, Bin Ma^a, Xi’an Li^a, Xinfu Pan^a, 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;

Abstract

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Abstract

(-)-Δ⁸-trans-Tetrahydrocannabinol was synthesized with high regio- and stereoselectivity through S_N2′ 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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