title: Total syntheses of (+)-vigulariol and (-)-sclerophytin A.
abstract: The total syntheses of (+)-vigulariol and (-)-sclerophytin A are reported in 15 steps and 16 steps, respectively, from a known compound. The flexible, readily scalable synthetic strategy allows for rapid construction of a critical tricyclic intermediate and is demonstrated via the synthesis of these two marine natural products. A key reaction in this synthetic protocol is a combination Wittig/intramolecular Diels-Alder cycloaddition.
authors.affiliation: Kenan Laboratory of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, USA. crimmins@email.unc.edu
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: Christina S
authors.initials: CS
authors.lastname: Stauffer
authors.forename: Mark C
authors.initials: MC
authors.lastname: Mans
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D001952:Bridged-Ring Compounds; D004224:Diterpenes; D004988:Ethers, Cyclic; D005663:Furans; C412667:sclerophytin A; C517746:vigulariol