PRODUCTION OF OUDEMANSIN, QUEBRACHITOL DERIVATIVE AS STARTING RAW MATERIAL FOR PRODUCTION OF OUDEMANSIN AND INTERMEDIATE THEREOF

摘要

PURPOSE: To produce the subject oudemansin exhibiting a strong antibacterial effect from a new quebrachitol derivative as the starting raw material through new intermediates. ;CONSTITUTION: The 3-4 bond of a quebrachitol derivative of formula I (R¹ is a divalent hydrocarbon group) is cut so as to form a linear compound and the terminal OH groups are each protected by an acyl group R³ to obtain a compound of formula II. The group R of the compound of formula II is eliminated so as to converted into an hydroxyl group and the C-C linkage bonded to the hydroxyl group is cut by oxidation. The resultant aldehyde is reduced to obtain a compound of formula III and the hydroxyl group of this compound is converted into a cyano group. The resultant compound of formula IV is deacylated and the obtained terminal alcohol is oxidized to an aldehyde. The resultant compound of formula V is converted into a compound of formula VI, e.g. by Wittig reaction. From this compound, the objective compound of formula VII (R² is phenyl, 4-methoxyphenyl or 3-methoxy-4- chlorophenyl) in which the partial structure composed of 9 to 10 positions corresponds to the three part structure composed of 5 to 6 positions of the compound of formula I can be obtained. The compounds of formulae II to IV and of formula VI are each a new substance.;COPYRIGHT: (C)1993,JPO&Japio