A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents


  • This work was supported by the National Institutes of Health (grant numbers: AI16943/CA28824/HL25848). L.J.W. gratefully acknowledges the NIH for a Postdoctoral Fellowship Grant (grant number: NIHF32CA79120). Prof. Gerard Parkin and Mr. Brian M. Bridgewater of Columbia University are gratefully acknowledged for the X-ray analysis.


The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine (1), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.

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