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

Lookup NU author(s): Dr Geoffrey Coxon, Professor David 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. © 2003 Elsevier Science Ltd. All rights reserved.

Publication metadata

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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