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Lookup NU author(s): Dr Geoffrey Coxon, Professor David Minnikin
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(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. © 2003 Elsevier Science Ltd. All rights reserved.
Author(s): Coxon GD, Al-Dulayymi JR, Baird MS, Knobl S, Roberts E, Minnikin DE
Publication type: Article
Publication status: Published
Journal: Tetrahedron: Asymmetry
Year: 2003
Volume: 14
Issue: 9
Pages: 1211-1222
ISSN (print): 0957-4166
ISSN (electronic): 1362-511X
Publisher: Pergamon
URL: http://dx.doi.org/10.1016/S0957-4166(03)00165-4
DOI: 10.1016/S0957-4166(03)00165-4
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