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James J. La Clair Total Syntheses of Hexacyclinol, 5-epi-Hexacyclinol, and Desoxohexacyclinol Unveil an Antimalarial Prodrug Motif Angewandte Chemie International Edition 45

Article first published online: 9 FEB 2006 | DOI: 10.1002/anie.200504033

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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.

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