title: Versatile solid-phase synthesis of chromenes resembling classical cannabinoids.
abstract: A novel solid-phase approach toward classical cannabinoids is described. The desired tricyclic natural product analogues are assembled in only four atom economic steps: domino oxa-Michael-aldol condensation, Wittig reaction/enol-ether formation, Diels-Alder cycloaddition and cleavage. The synthesis is designed to allow combinatorial chemistry at several stages of the sequence. The variation of commercially available reagents at three of the reactions (enals/enones, Wittig salts, and dienophiles) allows the introduction of various diversity points. As proof of concept, a small library of 20 members has been synthesized with overall yields ranging from 10% to 60%.
authors.affiliation: Karlsruhe Institute of Technology, Campus North, ComPlat, Eggenstein-Leopoldshafen, Germany.
authors.forename: Dagmar C
authors.initials: DC
authors.lastname: Kapeller
authors.forename: Stefan
authors.initials: S
authors.lastname: Bräse
mesh_terms: D001578:Benzopyrans / Q000737:chemistry*; D002186:Cannabinoids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D002186:Cannabinoids