Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone

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Abstract

Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The threo-isomer is the key precursor in the synthesis of the antibiotic clavalanine. © 1993.

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Ariza, J., Díaz, M., Font, J., & Ortuño, R. M. (1993). Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone. Tetrahedron, 49(6), 1315–1326. https://doi.org/10.1016/S0040-4020(01)85821-X

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