Tetrahedron: Asymmetry

(−)-Daucic acid: Proof of d-lyxo configuration, synthesis of its d-ribo, d-xylo, l-arabino and l-lyxo analogs, and biosynthetic implications

FW Lichtenthaler, J Klotz, K Nakamura

Index: Lichtenthaler, Frieder W.; Klotz, Juergen; Nakamura, Katsumi Tetrahedron Asymmetry, 2003 , vol. 14, # 24 p. 3973 - 3986

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Citation Number: 11

Abstract

The dimethyl esters of the 2, 6-anhydro-3-deoxy-hept-2-enaric acids with d-xylo, d-lyxo, l- arabino, l-lyxo-and d-ribo-configuration were synthesized from d-galactose and d-mannose, respectively, and further characterized by their di-O-acetyl and di-O-benzoyl derivatives. Comparison of their physical data with those of Daucus carota derived products revealed (−)- daucic acid to have d-lyxo-configuration 46 rather than the previously assigned d-xylo ...