title: Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: synthesis and configurational assignment of plakinic acid A.
abstract: The first asymmetric synthesis of 1,2-dioxolane-3-acetic acids is reported. Key features include the stereoselective opening of enantiomerically enriched oxetanes by hydrogen peroxide, conversion of the resulting 4-hydroperoxy-2-alkanols to 3-alkoxy-1,2-dioxolanes, and Lewis acid mediated homologation of the latter with a thioester silyl ketene acetal. The approach is modeled on 3,5-dimethyl-5-hexadecyl-1,2-dioxolane-3-acetic acid (1a), an unnamed natural product, and an optimized strategy is applied to the synthesis of four stereoisomers of plakinic acid A (2), allowing a configurational assignment of this incompletely characterized natural product.
authors.affiliation: Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68588-0304, USA.
authors.forename: Peng
authors.initials: P
authors.lastname: Dai
authors.forename: Tony K
authors.initials: TK
authors.lastname: Trullinger
authors.forename: Xuejun
authors.initials: X
authors.lastname: Liu
authors.forename: Patrick H
authors.initials: PH
authors.lastname: Dussault
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D004148:Dioxolanes; C516353:plakinic acid A