Four diastereomers of tetradenolide, a cytotoxic -pyrone isolated from Tetradenia riparia, were synthesized stereoselectively using Z-selective Horner-Emmons reaction followed by acid catalyzed lactonization. Making comparison of the 1 H and 13 C NMR spectral data of the four diastereomers with those of the reported value of natural product did not lead to determine the relative stereochemistry of the natural tetradenolide. Thus detailed investigation of the spectral data of the related compounds led us to revise the structure of tetradenolide as deacetylboronolide.
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