title: Stereoselective syntheses of cryptocarya diacetate and all its stereoisomers in optically pure forms.
abstract: Cryptocarya diacetate and each of its stereoisomers were stereoselectively synthesized in 8-16 steps. One of the three chiral carbons was converted from the chiral center of a yeast-reduction product. The other two chiral carbons were constructed by employing stereoselective allylation and syn-and anti-1,3-reductions. The enantiomeric excesses of the synthesized cryptocarya diacetate and its stereoisomers were determined to be more than 99%ee using a chiral column.
authors.affiliation: a Faculty of Agriculture , Ehime University , Matsuyama , Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
authors.forename: Hiroki
authors.initials: H
authors.lastname: Nishimura
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
mesh_terms: D000085:Acetates / Q000138:chemical synthesis*; D031369:Cryptocarya / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015003:Yeasts / Q000737:chemistry
chemical_list: D000085:Acetates; D011714:Pyrans; D011753:Pyrones
keywords: 6-substituted 5, 6-dihydropyran-2-one; Cryptocarya diacetate; Yeast-reduction product