- Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitor geldanamycin
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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 inhibitor geldanamycin, 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. The Royal Society of Chemistry 2007.
- McErlean, Christopher S. P.,Proisy, Nicolas,Davis, Christopher J.,Boland, Nicola A.,Sharp, Swee Y.,Boxall, Kathy,Slawin, Alexandra M. Z.,Workman, Paul,Moody, Christopher J.
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p. 531 - 546
(2008/03/27)
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- The Claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring benzoquinones including an ansa-bridged derivative related to the ansamycin antibiotics
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The naturally occurring benzoquinones primin 1 and pallasone B 2 were synthesised by a simple protocol involving microwave accelerated Claisen rearrangement of allyl ethers 4, followed by hydrogenation of the side chain alkene, and oxidation to the quinon
- Davis, Christopher J.,Moody, Christopher J.
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p. 1874 - 1876
(2007/10/03)
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