title: Differential use of anhydropyranosides for enantiopure routes to bis-gamma-butyrolactones: a new approach to the frameworks of antibiotic and anticancer agents isoavenaciolide and ethisolide.
abstract: Regio- and chemoselective syntheses of enantiopure bis-furanoids are described. These compounds are chirons for several families of bioactive natural products, including isoavenaciolide and ethisolide. Reaction of a 3,4-epoxy pyran with beta-ketoester dianions delivers substituted pyranosides in high yield. Cyclization then yields fused furan-pyran intermediates. Oxidation, deprotection, and rearrangement lead to bis-furanoids that bear the essential framework and stereochemistry of ethisolide and isoavenaciolide.
authors.affiliation: College of Pharmacy, University of Sharjah, P.O. Box 27272, Sharjah, UAE. taltal@sharjah.ac.ae
authors.forename: Taleb H
authors.initials: TH
authors.lastname: Al-Tel
authors.forename: Raed A
authors.initials: RA
authors.lastname: Al-Qawasmeh
authors.forename: Salim S
authors.initials: SS
authors.lastname: Sabri
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Voelter
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001230:Aspergillus / Q000302:isolation & purification; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D010407:Penicillium / Q000302:isolation & purification; D013237:Stereoisomerism; D053719:Tandem Mass Spectrometry
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D005663:Furans; D009005:Monosaccharides; C001168:ethisolide; D015107:4-Butyrolactone; C544632:isoavenaciolide