Inch, T. D., The Use of Carbohydrates

Inch, T. D., The Use of Carbohydrates in the Synthesis and Configurational Assignments of Optically Active, Non-carbohydrate Compounds, 27, 191-225... 

Inch, T D, The use of carbohydrates in the synthesis and configurational assignment of optically active non-carbohydrate compounds, Adv. Carbohydr. Chem. Biochem., 27, 191-225, 1972. 

For reviews see (a) R. J. Fenier and S. Middleton, The conversion of carbohydrates into functionalized cyclopentanes and cyclohexanes, Chem. Rev. 95 2779 (1993) (b) K. J. Hale, Monosaccharides Use in asymmetric synthesis of natural products, Rodd s Chemistry of Carbon Compounds. Second Supplement to the 2nd ed. (M. Sainsbury, ed.), Elsevier, Amsterdam, 1993, Vol. 1E/F/G, pp. 315-435 (c) T. D. Inch, Formation of convenient chiral intermediates from carbohydrates and their use in synthesis, Tetrahedron 40 3161 (1984) (d) S. Hanessian, Total Synthesis of Natural Products The Chiron Approach Pergamon, New York, 1983. 

However, it should be noted that the concept of carbohydrates as chiral synthons has always fascinated sugar chemists as the excellent 1972 review by Inch will attest 42). Thus in order to preserve historical perspective three antecedents for the use of sugars in asymmetric syntheses are noted in Scheme 1. First is Wolfrom s proof of the structure of (-t-)-alanine by synthesis from D-glucosamine 102). Second is the synthesis of the optically pure mandelic acid derivatives from 2,3-4,5-di-O-isopropylidene-fl/tfeAy o-D-arabinose (1) by Bonner (9), and third is Lemieux s synthesis of ethanol-l-d from diacetone glucose (6 a, Scheme 2) via the deuterated xylose (2) (57). 

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