title: A concise, convergent total synthesis of monocerin.
abstract: A concise and convergent eight-step synthesis of the antifungal metabolite monocerin 1 is reported. The key step involves an allylsilane metathesis/aldehyde condensation sequence to establish the core 2,3,5-trisubstituted tetrahydrofuran. End-game approaches based around intramolecular Heck chemistry revealed an interesting example of formal 6-endo cyclisation, the origin of which was probed using model substrates. The synthesis was ultimately completed by a strategy involving stepwise oxidative cleavage of the C3-ethenyl substituent.
authors.affiliation: Department of Chemistry, Imperial College, London, SW7 2AY, UK.
authors.forename: John H
authors.initials: JH
authors.lastname: Cassidy
authors.forename: Christopher N
authors.initials: CN
authors.lastname: Farthing
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Marsden
authors.forename: Anders
authors.initials: A
authors.lastname: Pedersen
authors.forename: Mark
authors.initials: M
authors.lastname: Slater
authors.forename: Geoffrey
authors.initials: G
authors.lastname: Stemp
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; C485193:monocerin