Preparation of optically active 4-demethoxydaunomycinone

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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260365, 260376, 549336, 568660, C07C 5036, C07C16702

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active

044951035

ABSTRACT:
A process for preparing optically active 4-demethoxy-7-deoxydaunomycinone which comprises reacting a racemic mixture of the .alpha.-hydroxyketone of the formula: ##STR1## with an optical isomer of the .alpha.-glycol of the formula: ##STR2## wherein R is a group of the formula: ##STR3## and X is a halogen atom or a lower alkyl group to give a diastereomeric mixture of the acetal of the formula: ##STR4## .

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Neuman, Tetrahedron Letters, No. 20, 1978, pp. 1709-1712, "Photochemistry of Phenyl Alkyl Ketones Under Pressure".
Plattner et al., Jol. of the American Chem. Soc., vol. 93, 1971, pp. 1758-1761, "The Synthesis of d & l-Sirenin and Their Absolute Configurations".
Rubin et al., Jol. of Amer. Chem. Soc., vol. 74, 1952, pp. 425-428, "Synthesis of the Optically Active Enantiomorphic 2,3-Butanediols".
Carmack et al., Jol. of Organic Chem., vol. 33, 1968, pp. 2171-2174, "The Synthesis of the Optically Active Cleland Reagent[(-)-1,4-Dithio-L.sub.g -threitol].

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