Stereoselective synthesis of 1-methyl-1,2-and 1,3-cyclopentanediols via γ-lactones

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

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2013-03, Vol.48 (12), p.1751-1760
Main Authors: Niidu, A., Paju, A., Müürisepp, A.-M., Järving, I., Kailas, T., Pehk, T., Lopp, M.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary:A method for the synthesis of 1-methylcarbapentofuranose derivatives was developed, where 1,2-cis- and 1,2-trans-4-hydroxymethyl-1-methylcyclopentanediols were obtained from intramolecular opening of a 4-epoxy-4-methyl-γ-lactone. An intramolecular aldol reaction of 4-methyl-4-(2-oxoethyl)-γ-lactone derivatives yielded 1,3-cis- and 1,3-trans-4-hydroxymethyl-1-methylcyclopentanediols.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-013-1206-4