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.
A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents
Article first published online: 27 OCT 2000
© 2000 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
Angewandte Chemie International Edition
Volume 39, Issue 21, pages 3866–3868, November 3, 2000
How to Cite
Wu, Z., Williams, Lawrence J. and Danishefsky, Samuel J. (2000), A Three-Step Entry to the Aspirochlorine Family of Antifungal Agents . Angew. Chem. Int. Ed., 39: 3866–3868. doi: 10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E
- Issue published online: 27 OCT 2000
- Article first published online: 27 OCT 2000
- Manuscript Received: 4 JUL 2000
- antifungal agents;
- natural products;
- sulfur heterocycles
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.