Issue 3, 2007

Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitorgeldanamycin

Abstract

A series of ansa-quinones has been prepared by chemical synthesis, and evaluated by biological techniques. Thus, 19-membered ansa-lactams, simplified analogues of the naturally occurring Hsp90 molecular chaperone inhibitorgeldanamycin, were obtained by concise routes, the key steps being the combination of a ring-closing metathesis to give a 17-membered ring followed by Claisen rearrangement to effect ring expansion. The methodology was also used to prepare an “unnatural” 18-membered ring analogue. In ATPase enzyme assays, the synthetic ansa-quinones were weak inhibitors of Hsp90.

Graphical abstract: Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitorgeldanamycin

Supplementary files

Article information

Article type
Paper
Submitted
23 Oct 2006
Accepted
04 Dec 2006
First published
04 Jan 2007

Org. Biomol. Chem., 2007,5, 531-546

Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitorgeldanamycin

C. S. P. McErlean, N. Proisy, C. J. Davis, N. A. Boland, S. Y. Sharp, K. Boxall, A. M. Z. Slawin, P. Workman and C. J. Moody, Org. Biomol. Chem., 2007, 5, 531 DOI: 10.1039/B615378J

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