Synthesis of a Thiashikimic Acid Derivative

Adam, David; Freer, Andrew A.; Isaacs, Neil W.; Kirby, Gordon W.; Littlejohn, Allison and Rahman, Mohammad S. (1992). Synthesis of a Thiashikimic Acid Derivative. Perkin Transactions 1: A Journal of Organic and Bio-Organic Chemistry, 10 pp. 1261–1264.

DOI: https://doi.org/10.1039/P19920001261

Abstract

6-Thiashikimic acid has been synthesised as its racemic ethyl ester acetate 10. Ethyl thioxoacetate 3, generated thermally from the anthracene cycloadduct 2, reacted with 1,4-diacetoxybuta- 1,3-diene 4 to give a pair of epimeric, Diels-Alder adducts 5 and 6. Each was converted with osmium tetroxide into the corresponding diol 7 and 8. The diol 7 underwent trans elimination of acetic acid in hot pyridine to give the 6-thiashikimic acid derivative 10. The configurations of both diols 7 and 8 were confirmed by X-ray crystal structure analysis. The conformations of the diols in the crystals and in solution are discussed in the light of their ¹H NMR spectra.

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