Structure of FR900452, a novel platelet-activating factor inhibitor from a Streptomyces

The Journal of Organic Chemistry
1987.0

Abstract

The structure of FR900452 (1) isolated from a Streptomyces as a potent inhibitor of platelet-activating factor has been deduced by using spectroscopic measurements and an X-ray crystal analysis of the dihydro derivative 2. The 5-(2-oxocyclopent-3-en-1-ylidene)-2-oxopiperazinyl skeleton of 1 is unique. Pyrolysis of N-tert-butylaziridines 1 in the presence of acetylenedicarboxylate gives adducts of structure 5, which rearrange to 6, rather than the expected ylide adducts 4.

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