215715-43-8Relevant articles and documents
Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products
Dion, Isabelle,Vincent-Rocan, Jean-Francois,Zhang, Lei,Cebrowski, Pamela H.,Lebrun, Marie-Eve,Pfeiffer, Jennifer Y.,Bedard, Anne-Catherine,Beauchemin, Andre M.
, p. 12735 - 12749 (2014/01/17)
Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.
The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4
Kerr, Daniel J.,Hamel, Ernest,Jung, M. Katherine,Flynn, Bernard L.
, p. 3290 - 3298 (2008/02/07)
A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converte
Total synthesis and evaluation of lamellarin α 20-Sulfate analogues
Ridley, Christian P,Reddy, M. Venkata Rami,Rocha, Genalyn,Bushman, Frederic D,Faulkner
, p. 3285 - 3290 (2007/10/03)
In order to explore the influence of sulfate groups on the bioactivity profiles of marine alkaloids of the lamellarin class, three such alkaloids, lamellarin α lamellarin α 13,20-disulfate and H, were synthesized and their activities against HIV-1 integrase and cancer cell ines were compared with those of lamellarin α 20-sulfate, which is a selective inhibitor of HIV-1 integrase. Lamellarin α does not inhibit HIV-1 integrase but shows moderate cytotoxicity with good cell line selectivity. Lamellarin α13,20-disulfate is a moderate inhibitor of both HIV-1 integrase and cancer cell lines. Lamellarin H is a more potent inhibitor of HIV-1 integrase but lacked the specificity required to be medicinally useful. Copyright
Synthesis, X-Ray Crystal Structure and Tubulin-Binding Properties of a Benzofuran Analogue of the Potent Cytotoxic Agent Combretastatin A4
Banwell, Martin G.,Flynn, Bernard L.,Willis, Anthony C.,Hamel, Ernest
, p. 767 - 774 (2007/10/03)
The benzofuran (4), a ring-fused analogue of the potent antimitotic agent combretastatin A4 (1), has been prepared by a convergent route involving 5-endo-dig iodocyclization of o-hydroxytolan (5) as the key step. Compound (4), which has been characterized crystallographically as well as spectroscopically, is inactive as a tubulin-binding agent.
