Advertisement

Total Syntheses of Hexacyclinol, 5-epi-Hexacyclinol, and Desoxohexacyclinol Unveil an Antimalarial Prodrug Motif

Authors

Errata

This article is corrected by:

  1. Errata: Retraction: Total Syntheses of Hexacyclinol, 5-epi-Hexacyclinol, and Desoxohexacyclinol Unveil an Antimalarial Prodrug Motif Volume 51, Issue 47, 11661, Article first published online: 14 November 2012

  • 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.

Abstract

original image

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.

Ancillary