483355-47-1Relevant academic research and scientific papers
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
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.
, p. 531 - 546 (2008/03/27)
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.
The Claisen rearrangement followed by phenol oxidation: A simple route to naturally occurring benzoquinones including an ansa-bridged derivative related to the ansamycin antibiotics
Davis, Christopher J.,Moody, Christopher J.
, p. 1874 - 1876 (2007/10/03)
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
