The synthesis of (11R,12S)-lactobacillic acid and its enantiomer

G.D. Coxon, J.R. Al Dulayymi, M.S. Baird, S. Knobl, E. Roberts, D.E. Minnikin

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Abstract

(11R,12S)-Lactobacillic acid has been prepared from 2,3-O-isopropylidene-d-glyceraldehyde, in a sequence involving asymmetric cyclopropanation, and from cis-cyclopropane-1,2-dimethanol, using enzymatic desymmetrisation. The key step in the former route was the stereochemically controlled cyclopropanation of (1Z,4′S)-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-1-octene via a Simmons–Smith type reaction, using diethylzinc and chloroiodomethane. This product was converted into the key intermediate (1R,2S)-1-formyl-2-hexylcyclopropane, which was also obtained by a known sequence from the (1R,2S)-monobutyrate ester of cis-cyclopropane-1,2-dimethanol. This pivotal aldehyde was converted into (11R,12S)-lactobacillic acid. Using analogous chemistry, the (11S,12R)-enantiomer of lactobacillic acid was prepared from 2,3-O-isopropylidene-d-glyceraldehyde or from the (1S,R)-monobutyrate ester of cis-cyclopropane-1,2-dimethanol.
Original languageEnglish
Pages (from-to)1211-1222
Number of pages12
JournalTetrahedron: Asymmetry
Volume14
Issue number9
DOIs
Publication statusPublished - 2003

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Keywords

  • lactobacillic acid
  • enantiomer
  • dimethanol

Cite this

Coxon, G. D., Al Dulayymi, J. R., Baird, M. S., Knobl, S., Roberts, E., & Minnikin, D. E. (2003). The synthesis of (11R,12S)-lactobacillic acid and its enantiomer. Tetrahedron: Asymmetry, 14(9), 1211-1222. https://doi.org/10.1016/S0957-4166(03)00165-4