title: Total synthesis of monosporascone and dihydromonosporascone.
abstract: The first total synthesis of monosporascone is presented. The five-step synthesis developed includes a silver acetylide-acid chloride coupling, domino Diels-Alder-retro-Diels-Alder reaction, and an intramolecular Friedel-Crafts acylation, and provides the natural product in 57% yield overall. Selective reduction of monosporascone also afforded the related metabolite dihydromonosporascone.
authors.affiliation: School of Chemistry and Biochemistry, The University of Western Australia, Perth, WA, Australia. matthew.piggott@uwa.edu.au.
authors.forename: Kathryn A
authors.initials: KA
authors.lastname: Punch
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Piggott
mesh_terms: D000215:Acylation; D001688:Biological Products / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*
chemical_list: D001688:Biological Products; D005663:Furans; D006571:Heterocyclic Compounds; D009285:Naphthoquinones