Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2017; 28(15): 1971-1974
DOI: 10.1055/s-0036-1588433
DOI: 10.1055/s-0036-1588433
letter
Total Synthesis of Cordyheptapeptide A
Further Information
Publication History
Received: 24 March 2017
Accepted: 01 May 2017
Publication Date:
31 May 2017 (online)
Abstract
The first total synthesis of cordyheptapeptide A is described. The synthesis is accomplished by a convergent approach featuring a combination of peptide coupling and the Ugi reaction for the preparation of the main building blocks and the acyclic precursor. The assembly of an N-methylated fragment by the Ugi reaction comprised the utilization of a convertible isonitrile followed by activation of the C-terminal amide. Two different macrocyclization sites were evaluated, proving greater efficacy the macrolactamization at the site Ile-Tyr, likely due of a more suitable conformational bias of the acyclic precursor having an internal β-turn centered at the N-Me-d-Phe-Pro moiety.
Key words
cordyheptapeptide - multicomponent reactions - cyclic peptides - convertible isonitrile - total synthesis - macrocyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588433.
- Supporting Information
-
References
- 1a Rukachaisirikul V. Chantaruk S. Tansakul C. Saithong S. Chaicharernwimonkoon L. Pakawatchai C. Isaka M. Intereya K. J. Nat. Prod. 2006; 69: 305
- 1b Isaka M. Srisanoh U. Lartpornmatulee N. Boonruangprapa T. J. Nat. Prod. 2007; 70: 1601
- 1c Chen Z. Song Y. Chen Y. Huang H. Zhang W. Ju J. Chatterjee J. Gilon C. Hoffman A. Kessler H. Brauch S. Henze M. Osswald B. Naumann K. Wessjohann LA. van Berkel SS. Westermann B. Bobach C. Schurwanz J. Franke K. Denkert A. Sung TV. Kuster R. Mutiso PC. Seliger B. Wessjohann LA. J. Nat. Prod. 2012; 75: 1215
- 2a Pando O. Stark S. Denkert A. Porzel A. Preusentanz R. Wessjohann LA. J. Am. Chem. Soc. 2011; 133: 7692
- 2b Tarman K. Lindequist U. Wende K. Porzel A. Arnold N. Wessjohann LA. Mar. Drugs 2011; 9: 294
- 2c Shabaan S. Ba LA. Abbas M. Burkholz T. Denkert A. Gohr A. Wessjohann LA. Sasse F. Weber W. Jacob C. Chem. Commun. 2009; 4702
- 2d Dömling A. Beck B. Eichelberger U. Sakamuri S. Menon S. Chen Q.-Z. Lu Y. Wessjohann LA. Angew. Chem. Int. Ed. 2006; 45: 7235
- 2e Bobach C. Schurwanz J. Franke K. Denkert A. Sung TV. Kuster R. Mutiso PC. Seliger B. Wessjohann LA. J. Ethnopharmacol. 2014; 155: 721
- 3a Dömling A. Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 3b Ugi I. Steinbrückner C. Chem. Ber. 1961; 94: 2802
- 4a Wessjohann LA. Morejón MC. Ojeda GM. Rhoden CR. B. Rivera DG. J. Org. Chem. 2016; 81: 6535
- 4b Neves RA. W. Westermann B. Wessjohann LA. Beilstein J. Org. Chem. 2011; 7: 1504
- 4c Neves RA. W. Stark S. Westermann B. Wessjohann LA. Beilstein J. Org. Chem. 2012; 8: 2085
- 4d Bauer SM. Armstrong RW. J. Am. Chem. Soc. 1999; 121: 6355
- 5a Morejón MC. Laub A. Westermann B. Rivera DG. Wessjohann LA. Org. Lett. 2016; 18: 4096
- 5b Hoffmann J. Gorges J. Junk L. Kazmaier U. Org. Biomol. Chem. 2015; 13: 6010
- 5c Rivera DG. Vasco AV. Echemendía R. Concepción O. Pérez CS. Gavín JA. Wessjohann LA. Chem. Eur. J. 2014; 20: 13150
- 6a Chatterjee J. Rechenmacher F. Kessler H. Angew. Chem. Int. Ed. 2013; 52: 254
- 6b Chatterjee J. Gilon C. Hoffman A. Kessler H. Acc. Chem. Res. 2008; 41: 1331
- 6c Chatterjee J. Rechenmacher F. Kessler H. Angew. Chem. Int. Ed. 2013; 52: 254
- 6d Wessjohann LA. Andrade CK. Z. Vercillo OE. Rivera DG. Targets Heterocycl. Syst. 2006; 10: 24
- 7 Coste J. Frerot E. Jouin P. J. Org. Chem. 1994; 59: 2437
- 8 Neves RA. W. Stark S. Morejon MC. Westermann B. Wessjohann LA. Tetrahedron Lett. 2012; 53: 5360
- 9a Spallarossa M. Wang Q. Riva R. Zhu J. Org. Lett. 2016; 18: 1622
- 9b van der Heijden G. Jong JA. W. Ruijter E. Orru RV. A. Org. Lett. 2016; 18: 984
- 9c Cioc CR. Preschel HD. van der Heijden G. Ruijter E. Orru RV. A. Chem. Eur. J. 2016; 22: 7837
- 9d Oikawa M. Sugamata Y. Chiba M. Fukushima K. Ishikawa Y. Synlett 2013; 24: 2014
- 9e Le HV. Fan L. Ganem BA. Tetrahedron Lett. 2011; 52: 2209
- 9f Pirrung MC. Ghorai S. Ibarra-Rivera TR. J. Org. Chem. 2009; 74: 4110
- 9g Gilley CB. Kobayashi Y. J. Org. Chem. 2008; 73: 4198
- 9h Kreye O. Westermann B. Wessjohann LA. Synlett 2007; 3188
- 9i Linderman RJ. Binet S. Petrich SR. J. Org. Chem. 1999; 64: 336
- 9j Lindhorst T. Bock H. Ugi I. Tetrahedron 1999; 55: 7411
- 9k Maison W. Schlemminger I. Westerhoff O. Martens J. Bioorg. Med. Chem. Lett. 1999; 9: 581
- 9l Keating TA. Armstrong RW. J. Am. Chem. Soc. 1996; 118: 2574