A considerable portion of this work was conducted during 1999–2002 at Bionic Bros GmbH, Germany. J.J.L.C. acknowledges the assistance of five technicians.
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Communication
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Total Syntheses of Hexacyclinol, 5-epi-Hexacyclinol, and Desoxohexacyclinol Unveil an Antimalarial Prodrug Motif†
Article first published online: 9 FEB 2006
DOI: 10.1002/anie.200504033
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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How to Cite
La Clair, J. J. (2006), Total Syntheses of Hexacyclinol, 5-epi-Hexacyclinol, and Desoxohexacyclinol Unveil an Antimalarial Prodrug Motif. Angew. Chem. Int. Ed., 45: 2769–2773. doi: 10.1002/anie.200504033
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Publication History
- Issue published online: 11 APR 2006
- Article first published online: 9 FEB 2006
- Manuscript Received: 14 NOV 2005
Corrected by:
Vol. 51, Issue 47, 11661, Article first published online: 14 NOV 2012
Keywords:
- antimalarial agents;
- medicinal chemistry;
- natural products;
- terpenoids;
- total synthesis
All sewn up: A “three-staged stitch” was used to append the A–C rings of desoxohexacyclinol (1), which was further converted into the related compounds hexacyclinol (2) and 5-epi-hexacyclinol (3). Screening of the late-staged intermediates indicated that precursors to 1 retain potent antimalarial activity. The mechanism of this action is suggested to involve a three-step prodrug-like activation.