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.
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.
Al-Tel
Taleb H
TH
College of Pharmacy, University of Sharjah, P.O. Box 27272, Sharjah, UAE. taltal@sharjah.ac.ae
Al-Qawasmeh
Raed A
RA
Sabri
Salim S
SS
Voelter
Wolfgang
W
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
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D005663:Furans; D009005:Monosaccharides; C001168:ethisolide; D015107:4-Butyrolactone; C544632:isoavenaciolide