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Lipase-mediated partial resolution of 1,2-diol and 2-alkanol derivatives: towards chiral building-blocks for pheromone synthesis

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
11
Issue
8
Identifiers
DOI: 10.1016/s0957-4166(00)00117-8
Keywords
  • Articles

Abstract

Abstract 1,2-Propanediol 5, 1-chloro-2-propanol 8 and its related 2- O-acetate 9 were partially resolved by chemoenzymatic acetylation and deacetylation, in the presence of Pseudomonas fluorescens lipase (Amano P.; PFL), to ( R)-(−)-1-acetoxy-2-propanol 6, ( R)-(+)-2-acetoxy-1-chloropropane 9 and ( R)-(−)-1-chloro-2-propanol 8, respectively. On the other hand, treatment of (2 RS)- 2 with vinyl acetate in ether and Chirazyme ® L-2 gave 2- O-acetyl-1,3,4-trideoxy-5,6:7,8-di- O-isopropylidene-β- d- manno-non-5-ulo-5,9-pyranose 1 and 1,3,4-trideoxy-5,6:7,8-di- O-isopropylidene-β- d- gluco-non-5-ulo-5,9-pyranose 11, respectively. Compound 10 was subsequently deacylated to 12. Both alcohols 11 and 12 were treated with Me 2CO/H + to cause their rearrangement to (2 S,5 R,8 R,9 R,10 S)-10-hydroxy-8,9-isopropylidenedioxy-2-methyl-1,6-dioxaspiro[4.5]decane 3 and its (2 R)-epimer 4, which closely matched the skeleton of the odour bouquet minor components of Paravespula vulgaris (L.).

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