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-00000084.xml
Synthesis 2016; 48(09): 1407-1413
DOI: 10.1055/s-0035-1561375
DOI: 10.1055/s-0035-1561375
paper
Two Novel and Simple Approaches to ‘CD45 Protein Tyrosine Phosphatase Inhibitor’ (Z)-Pulchellalactam and Derivatives
Further Information
Publication History
Received: 24 November 2015
Accepted after revision: 14 January 2016
Publication Date:
16 February 2016 (online)
Abstract
Two novel routes to the naturally occurring CD45 protein tyrosine phosphatase inhibitor, (Z)-pulchellalactam, and its derivatives are reported in two steps starting from dienoic acids through electrophilic cyclisation. This methodology proceeds regio- and stereoselectively, and can be used to design a library of synthetic pulchellalactam analogues.
Key words
dienoic acids - dienamides - iodocyclization - electrophilic cyclization - pulchellalactamSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561375.
- Supporting Information
-
References
- 1a Bew SP, Knight DW. Chem. Commun. (Cambridge) 1996; 1007
- 1b El-Taeb GM. M, Evans AB, Knight DW, Jones S. Tetrahedron Lett. 2001; 42: 5945
- 1c Sniady A, Wheeler KA, Dembinski R. Org. Lett. 2005; 7: 1769
- 2a Knight DW, Redfern AL, Gilmore J. J. Chem. Soc., Perkin Trans. 1 2001; 2874
- 2b Knight DW, Redfern AL, Gilmore J. J. Chem. Soc., Perkin Trans. 1 2002; 622
- 3a Ren X.-F, Turos E, Lake CH, Churchill MR. J. Org. Chem. 1995; 60: 6468
- 3b Ren X.-F, Konaklieva MI, Shi H, Dickey S, Lim DV, Gonzalez J, Turos E. J. Org. Chem. 1998; 63: 8898
- 4a Yue D, Larock RC. Org. Lett. 2004; 6: 1037
- 4b Barluenga J, Trincado M, Rubio E, Gonzalez JM. Angew. Chem. Int. Ed. 2003; 42: 2406
- 5a Banwell MG, Flynn BL, Wills AC, Hamel E. Aust. J. Chem. 1999; 52: 767
- 5b Arcadi A, Cacchi S, Fabrizi G, Marinelli F, Moro L. Synlett 1999; 1432
- 6a Flynn BL, Verdier-Pinard P, Hamel E. Org. Lett. 2001; 3: 651
- 6b Yue D, Larock RC. J. Org. Chem. 2002; 67: 1905
- 6c Hessian KO, Flynn BL. Org. Lett. 2003; 5: 4377
- 7a Huang Q, Hunter JA, Larock RC. J. Org. Chem. 2002; 67: 3437
- 7b Yao T, Larock RC. J. Org. Chem. 2003; 68: 5936
- 7c Bellina F, Biagetti M, Carpita A, Rossi R. Tetrahedron 2001; 57: 2857
- 7d Arcadi A, Cacchi S, Giuseppe SD, Fabrizi G, Marinelli F. Org. Lett. 2002; 4: 2409
- 7e Yue D, Della Ca N, Larock RC. Org. Lett. 2004; 6: 1581
- 8 Hessian KO, Flynn BL. Org. Lett. 2006; 8: 243 ; and references cited therein
- 9a Abarbri M, Parrain J.-L, Kitamura M, Noyori R, Duchêne A. J. Org. Chem. 2000; 65: 7475
- 9b Abarbri M, Parrain J.-L, Cintrat J.-C, Duchêne A. Synthesis 1996; 82
- 10 Rousset S, Thibonnet J, Abarbri M, Duchêne A, Parrain J.-L. Synlett 2000; 260
- 11 Cherry K, Thibonnet J, Duchêne A, Parrain J.-L, Abarbri M. Tetrahedron Lett. 2004; 45: 2063
- 12 Alvi KA, Casey A, Nair BG. J. Antibiot. 1998; 51: 515
- 13 Bolen JB, Thompsn PA, Eiseman E, Horak ID. Adv. Cancer Res. 1991; 57: 103
- 14a Gould KL, Moreno S, Tonks NK, Nurse P. Science 1990; 250: 1573
- 14b Koretzky GA, Picus J, Schultz T, Weiss A. Proc. Natl. Acad. Sci. U.S.A. 1991; 88: 2037
- 14c Weaver CT, Pingel JT, Nelson JO, Thomas ML. Mol. Cell. Biol. 1991; 11: 4415
- 14d Donovan JA, Koretzky GA. J. Am. Soc. Nephrol. 1993; 4: 976
- 15a Hooft van Huijsduijnen R. Gene 1998; 225: 1
- 15b Trowbridge JS. J. Biol. Chem. 1991; 266: 23571
- 15c Janeway CA. Annu. Rev. Immunol. 1994; 12: 85
- 15d Neel BG. Curr. Opin. Immunol. 1997; 9: 405
- 16 Li W.-R, Lin ST, Hsu N.-M, Chem M.-S. J. Org. Chem. 2002; 67: 4702
- 17 Bryans JS, Chessum NE. A, Huther N, Parsons AF, Ghelfi F. Tetrahedron 2003; 59: 6221
- 18 Mangaleswaran S, Argade NP. Synthesis 2004; 1560
- 19 Bessho J.-I, Shimotsu Y, Mizumoto S, Mase N, Yoda H, Takabe K. Heterocycles 2004; 63: 1013
- 20 Hermet JP, Caubert V, Langlois N. Synth. Commun. 2006; 36: 2253
- 21 Felluga F, Ghelfi F, Pagnoni UM, Parsons AF, Pattarozzi M, Roncaglia F, Valentin E. Synthesis 2007; 1882
- 22 Chavan SP, Pathak AB, Dhawane AN, Kalkote UR. Synth. Commun. 2007; 37: 1503
- 23a Stille JK. Angew. Chem., Int. Ed. Engl. 1986; 25: 508
- 23b Farina V, Krishnan B. J. Am. Chem. Soc. 1991; 113: 9585
- 23c Mitchell TN. Synthesis 1992; 803
- 24 Chong JM, Park SB. J. Org. Chem. 1993; 58: 523
- 25 Abarbri M, Parrain J.-L, Duchêne A. Synth. Commun. 1998; 28: 239
- 26a Sanz R, Pilar Castroviejo M, Guilarte V, Perez A, Fananas FJ. J. Org. Chem. 2007; 72: 5113
- 26b Jung ME. J. Org. Chem. 1992; 57: 3528
- 27 Thakkalapally A, Benin V. Tetrahedron 2005; 4939
- 28a Goh W, Iskander G, St Black D, Kumar N. Tetrahedron Lett. 2007; 48: 2287
- 28b Gupton JT, Telang N, Banner EJ, Kluball EJ, Hall KE, Finzel KL, Jia X, Bates SR, Welden RS, Giglio BC, Eaton JE, Barelli PJ, Firich LT, Stafford JA, Coppock MB, Worrall EF, Kanters RP. F, Keertikar K, Osterman R. Tetrahedron 2010; 66: 9113
- 29 Pittet AO, Klaiber EM. J. Agric. Food Chem. 1975; 23: 1189
- 30 Chattapadhyay TK, Dureya P. J. Agric. Food Chem. 2006; 54: 2129
- 31 Bardili B, Marschall-Weyerstahl H, Weyerstahl P. Liebigs Ann. Chem. 1985; 275