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Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family
D.H. Dethe, , S. Mahapatra, S. Das, V. Kumar B.
Published in Royal Society of Chemistry
2015
Volume: 51
   
Issue: 14
Pages: 2871 - 2873
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. © The Royal Society of Chemistry 2015.
About the journal
JournalData powered by TypesetChemical Communications
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN13597345