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Abstract:
The fatty acid aglycones of two naturally occurring glycosides, one of which is reported to possess antitumor activity, were synthesized for biological evaluation. The preparation of 3,11-dihydroxyhexadecanoic acid and 3,12-dihydroxyhexadecanoic acid started with the monoethyl esters of nonanedioic acid and decanedioic acid, respectively, and proceeded through the corresponding C14 ketoesters, ketalesters, and ketalaldehydes and C16 ketalhydroxyesters and dihydroxyesters. Various products and intermediates were found to have no inhibitory action in the P388 lymphocytic leukemia screen. A rearrangement of the ethylene glycol ketal-protecting group from the initially protected ketone group to a newly formed aldehyde moiety was observed.