title: Asymmetric total synthesis of (+)-O-methylasparvenone, a rare nitrogen-free serotonin 2C receptor antagonist.
abstract: The first enantioselective synthesis of the fungal metabolite (+)-O-methylasparvenone was achieved in eight steps and 22% overall yield from inexpensive 3,4,5-trimethoxybenzaldehyde dimethyl acetal. Key steps include (i) early-stage asymmetric alkynylation of an aromatic aldehyde with a propiolate, (ii) intramolecular Friedel-Crafts acylation, and (iii) site-selective cleavage of an aryl methyl ether.
authors.affiliation: Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval, 1045 Avenue de la Médecine, Quebec City, Quebec G1 V 0A6, Canada. john.boukouvalas@chm.ulaval.ca.
authors.forename: Raphaël
authors.initials: R
authors.lastname: Lafleur-Lambert
authors.affiliation: Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval, 1045 Avenue de la Médecine, Quebec City, Quebec G1 V 0A6, Canada. john.boukouvalas@chm.ulaval.ca.
authors.forename: John
authors.initials: J
authors.lastname: Boukouvalas
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry; D000215:Acylation; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D001547:Benzaldehydes / Q000138:chemical synthesis / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D005658:Fungi / Q000737:chemistry; D008745:Methylation; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D058830:Serotonin 5-HT2 Receptor Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000447:Aldehydes; D001547:Benzaldehydes; D009284:Naphthols; C111197:O-methylasparvenone; D058830:Serotonin 5-HT2 Receptor Antagonists