title: Synthesis of the A-D Ring System of the Gambieric Acids.
abstract: The A-D fragment of gambieric acids A and C has been synthesized using an asymmetric Tsuji-Trost allylation reaction to couple the two key segments. The A ring fragment has been prepared by a short and highly efficient route involving diastereoselective Lewis acid mediated alkylation of an acetal. Iterative ring-closing metathesis reactions have been used to construct cyclic ethers and assemble the tricyclic B-D fragment.
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow G12 8QQ, United Kingdom.
authors.forename: J Stephen
authors.initials: JS
authors.lastname: Clark
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow G12 8QQ, United Kingdom.
authors.forename: Filippo
authors.initials: F
authors.lastname: Romiti
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow G12 8QQ, United Kingdom.
authors.forename: Bora
authors.initials: B
authors.lastname: Sieng
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow G12 8QQ, United Kingdom.
authors.forename: Laura C
authors.initials: LC
authors.lastname: Paterson
authors.affiliation: School of Chemistry, University of Nottingham , University Park, Nottingham NG7 2RD, United Kingdom.
authors.forename: Alister
authors.initials: A
authors.lastname: Stewart
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow G12 8QQ, United Kingdom.
authors.forename: Subhabrata
authors.initials: S
authors.lastname: Chaudhury
authors.affiliation: WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow , University Avenue, Glasgow G12 8QQ, United Kingdom.
authors.forename: Lynne H
authors.initials: LH
authors.lastname: Thomas
mesh_terms: D000478:Alkylation; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D004141:Dinoflagellida / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D058116:Lewis Acids; C521443:gambieric acid C; D002922:Ciguatoxins; C080898:gambieric acid A; D010165:Palladium