By Robert P. Cook
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Extra resources for Cholesterol. Chemistry, Biochemistry, and Pathology
Best results are obtained with the benzoates (Nés et al, 1956). ( V ) is formed as a by-product in process b when 2,6-lutidine is used (Bernstein et al, 1949; Bide et al (1948a). (VI) is formed as a byproduct when collidine is used (Nés et al, 1956; Hunziker et al, 1955). t. (Tsuda et al, 1954). (d) H g ( O A c ) 2 in a solvent (EtOH, CC1 4, CHC1 3) containing AcOH with or without rx. (Windaus and Linsert, 1928 [ E ] ; Bergmann and Stevens, 1948 [E]; Antonucci et al, 1951; Nés et al, 1956). (e) H 2-Raney Ni-C 6H 6 (Anderson et al, 1952 [ E ] ; Heusser et al, 1951, footnotes p.
The structural relationship of the sterols and the bile acids was realized quite early, and to a large extent the structures assigned to the two classes of compounds are based on interrelated evidence. This evidence and the arguments used have been summarized elsewhere (Fieser and Fieser, 1949; Shoppee and Shoppee, 1953; Georg, 1954) and only a very brief account is warranted here. The progress of steroid research has recently been reviewed by Shoppee ( 1 9 5 6 ) . A. T H E DETERMINATION OF THE STRUCTURE OF CHOLESTEROL The work of Mauthner, Diels, Windaus, and Wieland in the first quarter of the century on the purely chemical degradation of cholesterol had led to the promulgation in 1928 of the first (incorrect) formula for cholesterol.
0 H 2-Pt-Et 20-AcOH (Schenck et al, 1936; Heilbron and Wilkinson, 1932). (/) H 2-Pt-EtOAc (Wieland et al, 1941). (k) HCI-CHCI3, KOH (to dehydrochlorinate the hydrochloride formed) (Wieland and Benend, 1942). 38 R - Q H n , R ' - H , Ac, or Bz PETER BLADON CHEMISTRY Ε. 39 CHOLESTADIEN- AND TRDZN-OLS (a) NBS or NBP in a solvent (CC1 4 or petrol) rx. with illumination with visible light. The product ( I I ) is probably the 7a-bromo compound (X = Br). (h) Tertiary amine (PhNMe 2, Py, or collidine ) rx.