Total synthesis of kapakahine E and F.

作者: Vinson R. Espejo , Jon D. Rainier

DOI: 10.1021/OL100672Z

关键词:

摘要: The total synthesis of the cyclic peptides kapakahine E and F using bromopyrroloindoline heterodimerization reactions, indoline to α-carboline rearrangements, Negishi coupling reactions is described.

参考文章(20)
Ryuichi Sakai, Tatsuki Koike, Makoto Sasaki, Keiko Shimamoto, Chie Oiwa, Atsuko Yano, Katsuji Suzuki, Kazuo Tachibana, Hisao Kamiya, Isolation, Structure Determination, and Synthesis of Neodysiherbaine A, a New Excitatory Amino Acid from a Marine Sponge Organic Letters. ,vol. 3, pp. 1479- 1482 ,(2001) , 10.1021/OL015798L
Vinson R. Espejo, Jon D. Rainier, An Expeditious Synthesis of C(3)−N(1′) Heterodimeric Indolines Journal of the American Chemical Society. ,vol. 130, pp. 12894- 12895 ,(2008) , 10.1021/JA8061908
Yoichi Nakao, Jacqueline Kuo, Wesley Y. Yoshida, Michelle Kelly, Paul J. Scheuer, More kapakahines from the marine sponge Cribrochalina olemda. Organic Letters. ,vol. 5, pp. 1387- 1390 ,(2003) , 10.1021/OL026830U
Andrew J. Ross, Hannah L. Lang, Richard F. W. Jackson, Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides. Journal of Organic Chemistry. ,vol. 75, pp. 245- 248 ,(2010) , 10.1021/JO902238N
Kazuo Sato, Alan P. Kozikowski, Construction of optically pure tryptophans from serine derived aziridine-2-carboxylates Tetrahedron Letters. ,vol. 30, pp. 4073- 4076 ,(1989) , 10.1016/S0040-4039(00)99325-0
Céline Mothes, Solange Lavielle, Philippe Karoyan, Amino-Zinc-Ene-Enolate Cyclization: A Short Access to cis-3-Substituted Prolino-homotryptophane Derivatives Journal of Organic Chemistry. ,vol. 73, pp. 6706- 6710 ,(2008) , 10.1021/JO801006A
Peter J. Harrington, Louis S. Hegedus, Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approaches to ergot alkaloids Journal of Organic Chemistry. ,vol. 49, pp. 2657- 2662 ,(1984) , 10.1021/JO00189A001
Carlos Pérez-Balado, Ángel R. de Lera, Expedient total syntheses of WIN 64745 and WIN 64821. Organic Letters. ,vol. 10, pp. 3701- 3704 ,(2008) , 10.1021/OL8013073
Elena Angelini, Cesarino Balsamini, Francesca Bartoccini, Simone Lucarini, Giovanni Piersanti, Switchable Reactivity of Acylated α, β-Dehydroamino Ester in the Friedel−Crafts Alkylation of Indoles by Changing the Lewis Acid The Journal of Organic Chemistry. ,vol. 73, pp. 5654- 5657 ,(2008) , 10.1021/JO800881U
Bryan K. S. Yeung, Yoichi Nakao, Robin B. Kinnel, John R. Carney, Wesley Y. Yoshida, Paul J. Scheuer, Michelle Kelly-Borges, The Kapakahines, Cyclic Peptides from the Marine Sponge Cribrochalina olemda Journal of Organic Chemistry. ,vol. 61, pp. 7168- 7173 ,(1996) , 10.1021/JO960725E