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4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of gamma-Alkylidenetetronic Acids

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Details

Original languageEnglish
Pages (from-to)836-840
Number of pages5
JournalZeitschrift fur Naturforschung Section B: A Journal of Chemical Sciences
Volume68
Issue number7
DOIs
Publication statusPublished - Jul 2013
Publication typeA1 Journal article-refereed

Abstract

A new approach to gamma-alkylidenetetronic acids is reported which is based on Me3SiOTf-catalyzed [3 + 2] cyclization of 4-tert-butoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with oxalyl chloride, orthogonal protection of the alpha-hydroxy group by benzylation and subsequent deprotection of the beta-hydroxy group.

Keywords

  • Butenolides, Cyclizations, O-Heterocycles, Oxalic Acid, Silyl Enol Ethers, CROSS-COUPLING REACTIONS, STEREOSELECTIVE-SYNTHESIS, EFFICIENT SYNTHESIS, ASCORBIC-ACID, ALKYLIDENEBUTENOLIDES, CYCLIZATION, CHEMISTRY, ETHERS