title: A formal synthesis of (-)-cyanolide A featuring a stereoselective Mukaiyama aldol reaction and oxocarbenium reduction.
abstract: The formal synthesis of the marine natural product (-)-cyanolide A is presented. The synthetic strategy is centered on two acyclic diastereoselective reactions and a single cyclic reaction with modest to excellent dr based on an initial stereocenter. Most notable is a highly stereoselective oxocarbenium reduction based on a "mismatched" reactive conformer to afford the β-C-glycoside subunit leading to an efficient synthesis of the diolide aglycon in 12 overall steps.
authors.affiliation: Department of Chemistry, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487-0336, United States.
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Sharpe
authors.forename: Michael P
authors.initials: MP
authors.lastname: Jennings
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000447:Aldehydes; D018942:Macrolides; C548188:cyanolide A; D002244:Carbon; C116609:3-hydroxybutanal