title: A unified approach to polyene macrolides: synthesis of candidin and nystatin polyols.
abstract: Polyene macrolide antibiotics are naturally occurring antifungal agents. Members of this class include amphotericin B, which has been used widely to treat systemic fungal infections. A general synthetic strategy has been devised to prepare polyol chains associated with the polyene macrolides. Cyanohydrin acetonide alkylations were used to assemble the carbon skeleton, and a simple modification of the strategy allowed an advanced intermediate to be converted to either the candidin polyol or the nystatin polyol. The candidin polyol was further elaborated to a protected candidin aglycone. This strategy will be applicable to other members of the polyene macrolide natural products.
authors.affiliation: Department of Chemistry, University of California, Irvine, CA 92697-2025, USA.
authors.forename: Isao
authors.initials: I
authors.lastname: Kadota
authors.forename: Yueqing
authors.initials: Y
authors.lastname: Hu
authors.forename: Garrick K
authors.initials: GK
authors.lastname: Packard
authors.forename: Scott D
authors.initials: SD
authors.lastname: Rychnovsky
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009761:Nystatin / Q000138:chemical synthesis* / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000935:Antifungal Agents; D018942:Macrolides; D011090:Polyenes; D009761:Nystatin; C010428:candidin