Download PDF
Synthesis 1988; 1988(11): 891-893
DOI: 10.1055/s-1988-27741
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Convenient Synthesis of Chiral Pyranones from Carbohydrates

Griselda M. De Fina* , Oscar Varela, Rosa M. de Lederkremer
  • *Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 1428 Buenos Aires, Argentina
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

2-Acyloxyglycals (2-O-acyl-1,5-anhydrohex-1-enitols) having a D-arabino configuration (1a, b) react highly stereoselectively with alcohols in the presence of a stoichiometric amount of tin(IV) chloride at 0-5°C to (2S, 6S)-6-acyloxymethyl-2-alkoxy-2H-pyran-3 (6H)-ones 2 together with furaldehyde by-products 3. In the case of 2-acyloxyglycals having a D-lyxo (1c, d) or an L-lyxo (4) configuration, reaction occurs readily at - 20°C to form the desired pyranones 2 or 5 without the formation of furaldehydes. All reactions showed high stereoselectivity for α-anomers in the formation of the acetal linkage, except the reaction of the tri-O-benzoyl derivative 1d with methanol. The method reported allows the synthesis of chiral pyranones in higher yield and by a shorter route than the previously reported methods.

      >