Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: Synthesis and configurational assignment of plakinic acid A

Peng Dai, Tony K. Trullinger, Xuejun Liu, Patrick H. Dussault

Research output: Contribution to journalArticle

45 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)2283-2292
Number of pages10
JournalJournal of Organic Chemistry
Volume71
Issue number6
DOIs
StatePublished - Mar 17 2006

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Biological Products
Dioxolanes
Acetates
Lewis Acids
Acetals
Stereoisomerism
Acetic Acid
Hydrogen Peroxide
formal glycol
plakinic acid A
oxetane
alkoxyl radical
ketene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Asymmetric synthesis of 1,2-dioxolane-3-acetic acids : Synthesis and configurational assignment of plakinic acid A. / Dai, Peng; Trullinger, Tony K.; Liu, Xuejun; Dussault, Patrick H.

In: Journal of Organic Chemistry, Vol. 71, No. 6, 17.03.2006, p. 2283-2292.

Research output: Contribution to journalArticle

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