title: A novel route to the vinyl sulfide nine-membered macrocycle moiety of Griseoviridin.
abstract: The synthetic potentialities of cerium(III) chloride are demonstrated by the synthesis of a nine-membered ring heterocycle component of Griseoviridin (3) in optically active form. The key step involves the stereospecific formation of the alpha-carbalkoxy alkenyl sulfide moiety using a combination system of cerium(III) chloride heptahydrate and sodium iodide.
authors.affiliation: Dipartimento di Scienze Chimiche, Camerino (MC), Italy. enricom@camserv.unicam.it
authors.forename: E
authors.initials: E
authors.lastname: Marcantoni
authors.forename: M
authors.initials: M
authors.lastname: Massaccesi
authors.forename: M
authors.initials: M
authors.lastname: Petrini
authors.forename: G
authors.initials: G
authors.lastname: Bartoli
authors.forename: M C
authors.initials: MC
authors.lastname: Bellucci
authors.forename: M
authors.initials: M
authors.lastname: Bosco
authors.forename: L
authors.initials: L
authors.lastname: Sambri
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002563:Cerium / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010455:Peptides; D012974:Sodium Iodide / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D014769:Virginiamycin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D006571:Heterocyclic Compounds; D010455:Peptides; D013440:Sulfides; D014769:Virginiamycin; D002563:Cerium; C010583:griseoviridin; D012974:Sodium Iodide; C026690:cerous chloride