656809-46-0Relevant academic research and scientific papers
Compositions And Methods Comprising Analogues Of Radicicol A
-
Page/Page column 43, (2010/09/18)
Disclosed are novel analogues of the natural product radicicol A of formulae I, .Ia, pi, Ha, lib and HI, pharmaceutical compositions comprising the compounds. The compounds of the invention are kinase and phosphatase inhibitors and find utility in the tre
Preparation, modification, and evaluation of cruentaren a and analogues
Bindl, Martin,Jean, Ludovic,Herrmann, Jennifer,Mueller, Rolf,Fuerstner, Alois
scheme or table, p. 12310 - 12319 (2010/05/02)
An expeditious total synthesis of the highly cytotoxic F-ATPase inhibitor cruentaren A. (1) is described based on a. ring-closing alkyne metathesis (RCAM) reaction for the formation of the macrocylic ring. Other key transformations comprise a. C-acylation
Concise total synthesis of cruentaren A
Fuerstner, Alois,Bindl, Martin,Jean, Ludovic
, p. 9275 - 9278 (2008/12/22)
Converging on the target: The highly cytotoxic F-ATPase inhibitor cruentaren A constitutes an interesting lead in the quest for innovative chemotherapeutic agents for the treatment of various diseases, including cancer. Its synthesis was achieved in an overall yield of 3% by an expeditious convergent route involving a ring-closing aikyne metathesis reaction (RCAM) for the formation of the macrocyclic ring (see picture). (Chemical Equation Presented)
Total synthesis of (S)-(+)-citreofuran by ring closing alkyne metathesis
Fuerstner, Alois,Castanet, Anne-Sophie,Radkowski, Karin,Lehmann, Christian W.
, p. 1521 - 1528 (2007/10/03)
A concise total synthesis of citreofuran 4 is described, a structurally unique octaketide derivative belonging to the curvularin family. Key steps involve the elaboration of orsellinic acid methyl ester 5 to acid 14, which converts, on attempted formation of the corresponding acid chloride, to the 3-alkoxyisocoumarin derivative 20. This heterocycle can be used as an activated ester to give ketone 21 on treatment with 3-pentynylmagnesium bromide in the presence of TMSCl as the activating agent. Ring-closing alkyne metathesis (RCAM) of diyne 21 catalyzed by (tBuO)3W≡CCMe3 affords the strained cycloalkyne 22. Treatment with acid renders its triple bond susceptible to nucleophilic attack by the adjacent carbonyl group, thus leading to a transannular cycloaromatization with formation of the intact skeleton of citreofuran. An X-ray crystallographic study reveals conformational details about this natural product. Finally, it is shown that 4 as well as its protected precursor 23 are able to cleave double-stranded DNA under oxidative conditions.
