Efficient Synthesis of Key Intermediate Toward Liphagal Synthesis

REFERENCES

• Cantley , L. C. The phosphoinositide 3-kinase pathway . Science 2002 , 296 , 1655 – 1657 .
   PubMed Web of Science ®Google Scholar
• Hayakawa , M. ; Kawaguchi , K. ; Kaizawa , H. ; Koizumi , T. ; Ohishi , T. ; Yamano , M. ; Okada , M. ; Ohta , M. ; Tsukamoto , S. ; Raynaud , F. I. ; Parker , P. ; Workman , P. ; Waterfield , M. D. Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110alpha inhibitors . Bioorg. Med. Chem. 2007 , 15 , 5837 – 5844 .
   PubMed Web of Science ®Google Scholar
• Ward , S. ; Sotsios , Y. ; Dowden , J. ; Bruce , I. ; Finan , P. Therapeutic potential of phosphoinositide 3-kinase inhibitors. Chem. Biol. 2003, 10, 207–213.
   PubMed Web of Science ®Google Scholar
• Ward , S. G. ; Finan , P. Isoform-specific phosphoinositide 3-kinase inhibitors as therapeutic agents . Curr. Opin. Pharmacol. 2003 , 3 , 426 – 434 .
   PubMed Web of Science ®Google Scholar
• Workman , P. Inhibiting the phosphoinositide 3-kinase pathway for cancer treatment . Biochem. Soc. Trans. 2004 , 32 , 393 – 396 .
   PubMed Web of Science ®Google Scholar
• Vanhaesebroeck , B. ; Leevers , S. J. ; Ahmadi , K. ; Timms , J. ; Katso , R. ; Driscoll , P. C. ; Woscholski , R. ; Parker , P. J. ; Waterfield , M. D. Synthesis and function of 3-phosphorylated inositol lipids . Annu. Rev. Biochem. 2001 , 70 , 535 – 602 .
   PubMed Web of Science ®Google Scholar
• Domin , J. ; Waterfield , M. D. Using structure to define the function of phosphoinositide 3-kinase family members . FEBS Lett. 1997 , 410 , 91 – 95 .
   PubMed Web of Science ®Google Scholar
• Knight , Z. A. ; Gonzalez , B. ; Feldman , M. E. ; Zunder , E. R. ; Goldenberg , D. D. ; Williams , O. ; Loewith , R. ; Stokoe , D. ; Balla , A. ; Toth , B. ; Balla , T. ; Weiss , W. A. ; Williams , R. L. ; Shokat , K. M. A pharmacological map of the PI3-K family defines a role for p110α in insulin signaling . Cell 2006 , 125 , 733 – 747 .
   PubMed Web of Science ®Google Scholar
• Engelman , J. A. ; Luo , J. ; Cantley , L. C. The evolution of phosphatidylinositol 3-kinases as regulators of growth and metabolism . Nat. Rev. Genet. 2006 , 7 , 606 – 619 .
   PubMed Web of Science ®Google Scholar
• Powis , G. ; Ihle , N. ; Kirkpatrick , D. L. Practicalities of drugging the phosphatidylinositol-3-kinase/Akt cell survival signaling pathway . Clin. Cancer Res. 2006 , 12 , 2964 – 2966 .
   PubMed Web of Science ®Google Scholar
• Ruckle , T. ; Schwarz , M. K. ; Rommel , C. PI3Kγ inhibition: towards an “aspirin of the 21st century”? Nat. Rev. Drug Discov. 2006 , 5 , 903 – 918 .
   PubMed Web of Science ®Google Scholar
• Hayakaa , M. ; Kaizawa , H. ; Kawaguchi , K. I. ; Matsuda , K. ; Ishikawa , N. ; Koizumi , T. ; Yamanao , M. ; Ohta , M. U.S. Patent 6403588 , 2002 .
   Google Scholar
• Robertson , A. J. ; Jackson , S. ; Kenche , V. ; Yaip , C. ; Parbaharan , H. ; Thompson , P. Int. Patent Appl. WO 0181346 A2 , 2001 .
   Google Scholar
• Sadhu , C. ; Masinovsky , B. ; Dick , K. ; Sowell , G. C. ; Staunton , D. E. Essential role of phosphoinositide 3-kinase δ in neutrophil directional movement . J. Immunol. 2003 , 170 , 2647 – 2654 .
   PubMed Web of Science ®Google Scholar
• Marion , F. ; Williams , D. E. ; Patrick , B. O. ; Hollander , I. ; Mallon , R. ; Kim , S. C. ; Roll , D. M. ; Feldberg , L. ; Soest , R. V. ; Andersen , R. J. Liphagal, a selective inhibitor of PI3 kinase α isolated from the sponge akacoralliphaga: Structure elucidation and biomimetic synthesis . Org. Lett. 2006 , 6 , 321 – 324 .
   Web of Science ®Google Scholar
• Mehta , G. ; Likhite , N. S. ; Kumar , C. S. A. A concise synthesis of the bioactive meroterpenoid natural product (±)-liphagal, a potent PI3 K inhibitor . Tetrahedron Lett. 2009 , 50 , 5260 – 5262 .
   Web of Science ®Google Scholar