title: Syntheses of (-)-cryptocaryolone and (-)-cryptocaryolone diacetate via a diastereoselective oxy-Michael addition and oxocarbenium allylation.
abstract: The total syntheses of both (-)-cryptocaryolone and (-)-cryptocaryolone diacetate is presented herein. The usage of a diastereoselective oxy-Michael addition/benzylidene acetal formation coupled with a selective axial oxocarbenium allylation allowed for the preparation of the α-C-glycoside moiety present in the bicyclic bridged structure. In addition, the syn-1,3-diol of the linear portion was installed via a Wacker oxidation followed by a subsequent directed reduction of the appropriate homoallylic alcohol precursor.
authors: Department of Chemistry, The University of Alabama, 250 Hackberry Lane, Tuscaloosa, Alabama 35487-0336, United States.
authors: Aymara M M
authors: AM
authors: Albury
authors: Michael P
authors: MP
authors: Jennings
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000438:Alcohols; C438934:C-glycoside; D006027:Glycosides; D009005:Monosaccharides; D011753:Pyrones; C476918:cryptocaryolone; C542715:cryptocaryolone diacetate