Brønsted Acid Catalyzed Asymmetric Synthesis of <i>cis</i> ‐Tetrahydrocannabinoids**
Caroline Dorsch, Christoph Schneider
Abstract
Abstract We report herein the catalytic asymmetric cyclization of 1‐aryl terpenols to afford enantiomerically highly enriched Δ 9 ‐ cis ‐tetrahydrocannabinoid scaffolds in a single step. As powerful chiral catalysts strongly acidic imidodiphosphorimidates (IDPis) have been identified which furnish the products with good yields and excellent enantioselectivity. Upon MOM‐deprotection some naturally occurring cannabimimetica such as (−)‐ cis ‐ Δ 9 ‐tetrahydrocannabinol and (−)‐perrottetinene as well as some unnatural analogues were made accessible along a merely 3‐step biomimetic sequence (MOM=methoxymethyl).
Topics & Concepts
CatalysisBrønsted–Lowry acid–base theoryChemistryEnantioselective synthesisCombinatorial chemistryStereochemistrySequence (biology)Organic chemistryBiochemistrySynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisChemical synthesis and alkaloids