title: Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone.
abstract: A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paternò-Büchi [2 + 2] photocycloaddition from known enol ether 4, derived from the readily available sugar d-isosorbide, yielded oxetane 7. This slow, dilute reaction was scaled up by using flow photochemistry to yield >40 g of 7. Installation of the key lactone ring was achieved via a unique Wacker-style oxidation of an enol-ether bond. Acid-catalyzed aqueous ring opening provided 1 in five steps from 4 (11.5% overall).
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol, BS8 1TS, U.K.
authors.forename: Michael
authors.initials: M
authors.lastname: Ralph
authors.affiliation: Syngenta U.K., Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, U.K.
authors.forename: Sean
authors.initials: S
authors.lastname: Ng
authors.affiliation: School of Chemistry, University of Bristol , Cantock's Close, Bristol, BS8 1TS, U.K.
authors.forename: Kevin I
authors.initials: KI
authors.lastname: Booker-Milburn
mesh_terms: D002384:Catalysis; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004988:Ethers, Cyclic; D054335:Goniothalamus / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism
chemical_list: D003603:Cytotoxins; D004988:Ethers, Cyclic; D007783:Lactones; C073080:7-goniofufurone; C005287:oxetane