Reichstein-Grussner synthesis

Table 20.3 Features of the steps in the Reichstein-Grussner synthesis.

MgS04) it, filter it again and evaporate to give a yellow oil. Addition of one drop of H2O induces crystallisation to the monohydrate, which also forms rhombic crystals on recrystallisation from 95% EtOH/H20 at room temperature. [Flatt et al. Synthesis 815 1979, Reichstein Grussner Helv Chim Acta 17 311 1934, Takagi Jeffrey Acta Crystallogr Sect B 34 2932 1978, cf Org Synth 55 80 1976, Beilstein 19/12 V 520.]... 

Tadeus Reichstein (1897-1996), professor of Chemistry and director of the Pharmaceutical Institute, University of Basel (Switzerland), Nobel Prize in Physiology or Medicine 1950. As a major figure in the elucidation of the chemistry of steroids, his work will be encountered again (vide infra). The Haworth work was published in 1934 (Ault, R. G. Baird, D. K. Carrington, H. C Haworth, W. N. Herbert, R. Hirst, E. L. Percival, E. G. V. Smith, E Stacey, M. J. Chem. Soa, 1933,1419 while the full synthesis of Reichstein, T Grussner, A. Helv. Chim. Acta, 1934, 17, 311 and then Reichstein, T Grtissner, A. Oppenauer, R. appeared in Helv. Chim. Acta, 1934,77,510). 

Scheme 11.18. A representation of the Reichstein synthesis of L-ascorbic acid (Reichstein, T. Grussner, A. Helv. Chim. Acta, 1934,17,311). Note with regard to the structure of D-glucose as shown in the brackets, when the strncture is flipped 180°, the Rscher representation (where the groups on the horizontal are above the plane of the paper ) becomes reversed and would be below the plane. Thus, to preserve the absolute stereochemistry, the groups appear reversed in the drawing.

Reichstein T, Grussner A (1934) A productive synthesis of L-arcorbic acid (C-vitamin). Helv Chim Acta 17 311-328... 

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