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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 3
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Original Articles

A Regioselective Acylation of N‐Substituted‐4‐Aminoindole. Its Application to the Synthesis of Indolactam V

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Pages 523-531 | Received 14 Aug 2003, Published online: 16 Aug 2006

References

  • Moore , R. E. 1977 . Toxins from Blue‐Green Algae . Bioscience , 27 : 797
  • Schantz , E. J. , Lynch , J. M. , Vayvada , G. , Matsumoto , K. and Rapoport , H. 1966 . The purification and characterization of the poison produced by Gonyaulax catenella in axenic culture . Biochemistry , 5 : 1191 [PUBMED] [INFOTRIEVE]
  • Kishi , Y. and Rando , R. R. 1998 . Structural basis of protein kinase C activation by tumor promoters . Acc. Chem. Res. , 31 : 163 [CROSSREF]
  • Alvarez , M. and Salas , M. 1991 . Marine nitrogen‐containing heterocyclic natural products. Structures and syntheses of compounds containing quinoline and/or isoquinoline units . Heterocycles , 32 : 1391
  • Endo , Y. , Shudo , K. and Okamoto , T. 1982 . Molecular requirements for epigenetic modulators. Synthesis of active fragments of teolicidin and lyngbyatoxin . Chem. Pharm. Bull. , 30 : 3457
  • Lazlo , S. , Ley , S. V. and Porte , R. A. 1986 . Synthetic approaches to the teolicidin‐related tumor promoters: a total synthesis of (±)‐indolactam V . J. Chem. Soc. Chem. Commun. , : 344 [CROSSREF]
  • Nakatsuka , S. , Masuda , T. , Sakai , K. and Goto , T. 1986 . Synthetic studies of teolicidin IV. An efficient synthesis of (−)‐indolactam V . Tetrahedron Lett. , 27 : 5735 [CROSSREF]
  • Mascal , M. and Moody , C. J. 1988 . Synthesis of (−)‐indolactam . J. Chem. Soc. Chem. Commun. , : 589 [CROSSREF]
  • Muratake , H. and Natsume , M. 1987 . Total synthesis of lyngbyatoxin A (teolicidin A‐1) and teolicidin A‐2 . Tetrahedron Lett. , 20 : 2265 [CROSSREF]
  • Quick , J. , Saha , B. and Driedger , P. E. 1994 . Protein kinase C modulators. Indolactams 2. Alkylation of 4‐nitroindole by Grignard reagents. Synthesis of (−)‐7‐octylindolactam V . Tetrahedron Lett. , 35 ( 46 ) : 8549 [CROSSREF]
  • Messeguer , B. , Alonso‐Díaz , D. , Griebenow , N. , Herget , H. and Waldman , H. 1999 . Natural product synthesis on polymeric supports‐ synthesis and biological evaluation of an indolactam library . Angew. Chem. Int. Ed. , 38 : 2902 [CROSSREF]
  • Messeguer , B. , Alonso‐Díaz , D. , Griebenow , N. , Herget , H. and Waldman , H. 2000 . Solid‐phase synthesis and biological evaluation of a teolicidin library‐discovery of a selective PKCδ down regulator . Chem. Eur. J. , 6 : 3943 [CROSSREF]
  • Batcho , A. D. and Leimgruber , W. Indole derivatives and their intermediates . US Patent 3,732,245 . 1973 .
  • Batcho , A. D. and Leimgruber , W. Intermediates for Indoles . US Patent 3,976,639 . 1976 .
  • Kogan , T. P. , Somers , T. C. and Venuti , M. C. 1990 . Regio and stereocontrolled total synthesis of (−)‐indolactam V . Tetrahedron , 46 : 6623 [CROSSREF]
  • Compagnone , R. S. and Suárez , A. I. 1992 . Stereoselective synthesis of methoxy substituted 2,3‐dibenzylbutirolactones via organic phosphonates . Synth. Commun. , 22 : 3041
  • Suárez , A. I. , Lopez , F. and Compagnone , R. S. 1993 . Stereospecific synthesis of the lignans: 2‐S‐(3,4‐dimethoxybenzyl)‐3‐R‐(trimethoxybenzyl) butyrolactone, and its positional isomeric lactone . Synth. Commun. , 23 : 1991
  • Hosomi , A. , Hashimoto , H. and Sakurai , H. 1980 . 2‐alkoxy carbonylallyltrimethylsilanes as new reagents of 2‐alkoxycarbonyl allylation of electrophiles . Tetrahedron Lett. , 21 : 951 [CROSSREF]
  • Endo , Y. , Shudo , K. , Furuhata , K. , Sakai , S. , Aimi , N. , Hitotsuyunagi , Y. and Koyama , Y. 1984 . Synthesis of optically active teolicidin derivatives. Absolute configuration of teolicidin B and olivoretin A . Chem. Pharm. Bull. , 32 : 358
  • Xang , C. 1997 . The use Lewis acid in the reaction of zinc salts of indoles and acyl chlorides . Synth. Commun. , 7 ( 12 ) : 2125
  • Shinkai , I. 1997 . Regioselective synthesis of 3‐substituted indoles: 3‐ethylindole . Org. Syn. , 74 : 248
  • Arya , P. , Joseph , R. and Chou , D. 2002 . Toward high‐throughput synthesis of complex natural product‐like compounds in the genomic and proteomic age . Chem. Bio. , 9 : 145 [CSA] [CROSSREF]

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