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Total Syntheses of Hexacyclinol, 5‐ epi ‐Hexacyclinol, and Desoxohexacyclinol Unveil an Antimalarial Prodrug Motif
Author(s) -
La Clair James J.
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200504033
Subject(s) - prodrug , chemistry , stereochemistry , append , combinatorial chemistry , biochemistry , computer science , programming language
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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