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Preparation of O-methyl 3-acyl tetronic acids by the direct acylation of stannyl tetronates

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
30
Issue
8
Identifiers
DOI: 10.1016/s0040-4039(00)95301-2

Abstract

Abstract Formation of the 5-unsubstituted, O-methyl acyl tetronic acid nucleus found in tetronasin ( 1) has been achieved by the direct acylation of a 3-stanyl tetronate with a variety of acid chlorides in the presence of a palladium catalyst. Further functionalization of the tin tetronate at C-5 prior to acylation leads to the synthesis of the mould metabolite (±) dimethyl carolinic acid ( 12) and the 5-methylene tetronate nucleus found in tetronomycin ( 2).

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