title: Biomimetic Total Synthesis of (±)-Verrubenzospirolactone.
abstract: A five-step total synthesis of (±)-verrubenzospirolactone has been achieved using a biomimetic, intramolecular Diels-Alder reaction of a 2H-chromene to form two rings and four stereocenters in the final step. This Diels-Alder reaction occurs spontaneously at 30 °C "on-water", and thus suggests that it is likely to be non-enzymatic in nature. The structure of (±)-verrubenzospirolactone was also used to inspire a quadruple cascade reaction to generate seven stereocenters, four rings, three C-C bonds, and two C-O bonds in one step.
authors.affiliation: Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
authors.forename: Hiu C
authors.initials: HC
authors.lastname: Lam
authors.affiliation: Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
authors.forename: Henry P
authors.initials: HP
authors.lastname: Pepper
authors.affiliation: Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Sumby
authors.affiliation: Department of Chemistry, University of Adelaide, Adelaide, SA, 5005, Australia.
authors.forename: Jonathan H
authors.identifier: 0000-0002-7330-2160
authors.initials: JH
authors.lastname: George
keywords: biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis