STEREOSELECTIVE SYNTHESIS OF 1-METHYL-1,2- AND 1,3-CYCLOPENTANEDIOLS <i>via</i> γ-LACTONES

Authors

  • A. Niidu Cambrex Tallinn AS
  • A. Paju Tallinn University of Technology
  • A.-M. Müürisepp Tallinn University of Technology
  • I. Järving Tallinn University of Technology
  • T. Kailas Tallinn University of Technology
  • T. Pehk National Institute of Chemical Physics and Biophysics
  • M. Lopp Tallinn University of Technology

DOI:

https://doi.org/10.1007/846

Keywords:

carbaribose, cyclopentane-1, 2-diols, 3-diols, γ-lactone derivatives, oxabicyclo[2.2.1]heptanone, cyclization, epoxide opening

Abstract

A method for the synthesis of derivatives of 1-methylcarbapentofuranoses was developed. 1,2-cis- and 1,2-trans-4-hydroxymethyl-1-methylcyclopentanediols were obtained from intramolecular opening of 4-epoxy-4-methyl-γ-lactone. 1,3-cis- and 1,3-trans-4-hydroxymethyl-1-methylcyclopentanediols were obtained from intramolecular aldol reaction of 4-methyl-4-(2-oxoethyl)-γ-lactone derivatives.

Also published in Chemistry of Heterocyclic Compounds, 2013, 48 (12), pp 1751-1760

http://link.springer.com/article/10.1007/s10593-013-1206-4

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Published

2013-08-19

Issue

No. 12 (2012)

Section

Original Papers