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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 2
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Original Articles

Ionic‐Liquid‐Supported Total Synthesis of Sansalvamide A Peptide

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Pages 239-248 | Received 20 Jun 2006, Published online: 18 Jan 2008

References

  • Belofsky , G. N. , Jensen , P. R. and Fenical , W. 1999 . Sansalvamide: A new cytotoxic cyclic depsipeptide produced by a marine fungus of the genus Fusarium . Tetrahedron Lett. , 40 : 2913 – 2916 .
  • Liu , S. , Gu , W. , Lo , D. , Ding , X. Z. , Ujiki , M. , Adrian , T. E. , Soff , G. A. and Silverman , R. B. 2005 . N‐methylsansalvamide A peptide analogues. Potent new antitumor agents . J. Med. Chem. , 48 : 3630 – 3638 .
  • Hwang , Y. , Rowley , D. , Rhodes , D. , Gertsch , J. , Fenical , W. and Bushman , F. 1999 . Mechanism of inhibition of a poxvirus topoisomerase by the marine natural product Sansalvamide A . Molecular Pharmacology , 55 : 1049 – 1053 .
  • Lee , Y. and Silverman , R. B. 2000 . Rapid, high‐yield, solid‐phase synthesis of the antitumor antibiotic sansalvamide A using a side‐chain‐tethered phenylalanine building block . Org. Lett. , 2 : 3743 – 3746 .
  • Gu , W. X. , Liu , S. X. and Silverman , R. B. 2002 . Solid‐phase, Pd‐catalyzed silicon‐aryl carbon bond formation. Synthesis of sansalvamide A peptide . Org. Lett. , 4 : 4171 – 4174 .
  • Carroll , C. L. , Johnston , J. V. C. , Kekec , A. , Brown , J. D. , Parry , E. , Cajica , J. , Medina , I. , Cook , K. M. , Corral , R. , Pan , P. S. and McAlpine , S. R. 2005 . Synthesis and cytotoxicity of novel sansalvamide A derivatives . Org. Lett. , 7 : 3481 – 3484 .
  • Styers , T. J. , Rodriguez , R. , Pan , P. S. and McAlpine , S. R. 2006 . High‐yielding macrocyclization conditions used in the synthesis of novel Sansalvamide A derivatives . Tetrahedron Lett. , 47 : 515 – 517 .
  • Styers , T. J. , Kekec , A. , Rodriguez , R. , Brown , J. D. , Cajica , J. , Pan , P. S. , Parry , E. , Carroll , C. L. , Medina , I. , Corral , R. , Lapera , S. , Otrubova , K. , Pan , C. M. , McGuire , K. L. and McAlpine , S. R. 2006 . Synthesis of Sansalvamide A derivatives and their cytotoxicity in the MSS colon cancer cell line HT‐29 . Bioorg. Med. Chem. , 14 : 5625 – 5631 .
  • Otrubova , K. , McGuire , K. L. and McAlpine , S. R. 2007 . Scaffold targeting drug‐resistant colon cancers . J. Med. Chem. , 50 : 1999 – 2002 .
  • Rodriguez , R. A. , Pan , P. S. , Pan , C. M. , Ravula , S. , Lapera , S. , Singh , E. K. , Styers , T. J. , Brown , J. D. , Cajica , J. , Parry , E. , Otrubova , K. and McAlpine , S. R. 2007 . Synthesis of second‐generation sansalvamide A derivatives: Novel templates as potential antitumor agents . J. Org. Chem. , 72 : 1980 – 2002 .
  • Janus , E. , Goc‐Maciejewska , I. , Łożyński , M. and Pernak , J. 2006 . Diels–Alder reaction in protic ionic liquids . Tetrahedron Lett. , 47 : 4079 – 4083 .
  • Welon , T. 1999 . Room‐temperature ionic liquids. Solvents for synthesis and catalysis . Chem. Rev. , 99 : 2071 – 2083 .
  • Carmichael , A. J. , Earle , M. J. , Holbrey , J. D. , McCormac , P. B. and Seddon , K. R. 1999 . The Heck reaction in ionic liquids: A Multiphasic catalyst system . Org. Lett. , 1 : 997 – 1000 .
  • Mastrorilli , P. , Nobile , C. F. and Taccardi , N. 2006 . Chloride based ionic liquids as promoting agents for Meerwein reaction in solventless conditions . Tetrahedron Lett. , 47 : 4759 – 4762 .
  • Sheldon , R. 2001 . Catalytic reactions in ionic liquids . Chem. Commun. , : 2399 – 2407 .
  • Sheldon , R. A. , Lau , R. M. , Sorgedrager , M. J. , Rantwijk , F. V. and Seddon , K. R. 2002 . Biocatalysis in ionic liquids . Green Chem. , 4 : 147 – 151 .
  • Huang , J. Y. , Lei , M. and Wang , Y. G. 2006 . A novel and efficient ionic liquid supported synthesis of oligosaccharides . Tetrahedron Lett. , 47 : 3047 – 3050 .
  • Miao , W. and Chan , T. H. 2005 . Ionic‐liquid‐supported peptide synthesis demonstrated by the synthesis of Leu5‐enkephalin . J. Org. Chem. , 70 : 3251 – 3255 .
  • Yi , F. , Peng , Y. and Song , G. 2005 . Microwave‐assisted liquid‐phase synthesis of methyl 6‐amino‐5‐cyano‐4‐aryl‐2‐methyl‐4H‐pyran‐3‐carboxylate using functional ionic liquid as soluble support . Tetrahedron Lett. , 46 : 3931 – 3933 .
  • Kort , M. D. , Tuin , A. W. , Kuiper , S. , Overkleeft , H. S. , Marel , G. A. V. D. and Buijsman , R. C. 2004 . Development of a novel ionic support and its application in the ionic liquid phase assisted synthesis of a potent antithrombotic . Tetrahedron Lett. , 45 : 2171 – 2175 .

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