Issue 14, 2015

Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family

Abstract

A simple, highly diastereoselective, Lewis acid catalyzed Friedel–Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ8-THC, Δ9-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiomers has been achieved with high atom economy, in a protecting group free manner and in less than 6 steps, the longest linear sequence, in a very good overall yield starting from R-(+) and S-(−)-limonene.

Graphical abstract: Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family

Supplementary files

Article information

Article type
Communication
Submitted
29 Oct 2014
Accepted
02 Jan 2015
First published
05 Jan 2015
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2015,51, 2871-2873

Author version available

Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family

D. H. Dethe, R. D. Erande, S. Mahapatra, S. Das and V. K. B., Chem. Commun., 2015, 51, 2871 DOI: 10.1039/C4CC08562K

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