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Synthesis 2014; 46(11): 1506-1510
DOI: 10.1055/s-0033-1340988
DOI: 10.1055/s-0033-1340988
paper
An Efficient Synthesis of Katsube Nitrile: A Key Building Block for Eburnamine-Vincamine Alkaloids
Further Information
Publication History
Received: 13 January 2014
Accepted after revision: 21 February 2014
Publication Date:
26 March 2014 (online)
Abstract
A novel synthesis of the Katsube nitrile is achieved via an efficient diastereoselective Pictet–Spengler cyclization of 3-ethyl-2-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-6-oxopiperidine-3-carbonitrile to construct the cis-[CD] rings in 1-ethyl-4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carbonitrile, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed condensation of tert-butyl 4-cyano-4-(hydroxymethyl)hexanoate with tryptamine to assemble 4-cyano-4-(hydroxymethyl)-N-[2-(1H-indol-3-yl)ethyl]hexanamide as the key steps.
Key words
eburnamine-vincamine alkaloids - Katsube nitrile - Pictet–Spengler cyclization - cis-diastereoselectivity - 1,5,7-triazabicyclo[4.4.0]dec-5-eneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Saxton JE. Nat. Prod. Rep. 1996; 13: 327
- 1b Bonoczk P, Panezel G, Nagy Z. Eur. J. Ultrasound 2002; 15: 85
- 1c Horvath B, Marton Z, Ilalmosi S. Clin. Neuropharmacol. 2002; 25: 37
- 2a For reviews on synthesis of eburnamine-vincamine alkaloids, see: Atta-ur-Rahman, Sultana M. Heterocycles 1984; 22: 841
- 2b Sheng MH, Sun HB. Prog. Pharm. Sci. 2010; 34: 7
- 3a Pfaffli P, Oppolzer W, Wenger R, Hauth H. Helv. Chim. Acta 1975; 58: 1131
- 3b Klatte F, Rosentreter U, Winterfeldt E. Angew. Chem. 1977; 89: 916
- 3c Herrmann JL, Cregge RJ, Richman JE, Kieczykowski GR, Schlessinger RH. J. Am. Chem. Soc. 1979; 101: 1540
- 3d Takano S, Yonaga M, Ogasawara K. Heterocycles 1982; 19: 1391
- 3e Takano S, Yonaga M, Morimoto M, Ogasawara K. J. Chem. Soc., Perkin Trans. 1 1985; 305
- 4a Node M, Nagasawa H, Fuji K. J. Org. Chem. 1990; 55: 517
- 4b Meyers AI, Romine J, Robichaud AJ. Heterocycles 1990; 30: 339
- 4c Ihara M, Yasui K, Taniguchi N, Fukumoto K. Heterocycles 1990; 31: 1017
- 4d Gmeiner P, Feldman PL, Chu-Moyer MY, Rapoport H. J. Org. Chem. 1990; 55: 3068
- 4e Schultz AG, Pettus L. J. Org. Chem. 1997; 62: 6855
- 4f Wee AG. H, Yu Q. Tetrahedron Lett. 2000; 41: 587
- 4g Wee AG. H, Yu Q. J. Org. Chem. 2001; 66: 8935
- 4h Tanino H, Fukuishi K, Ushiyama M, Okada K. Tetrahedron 2004; 60: 3273
- 4i Hayashi M, Motosawa K, Satoh A, Shibuya M, Ogasawara K, Iwabuchi Y. Heterocycles 2009; 77: 855
- 5a Ono K, Kawakami H, Katsube J. Heterocycles 1980; 14: 411
- 5b Christie BD, Rapoport H. J. Org. Chem. 1985; 50: 1239
- 5c Langlois Y, Pouilhes A, Genin D, Andriamialisoa RZ, Langlois N. Tetrahedron 1983; 39: 3755
- 6 Ono N, Yoshimura T, Saito T, Tamura R, Tanikaga R, Kaji A. Bull. Chem. Soc. Jpn. 1979; 52: 1716
- 7 Starkov P, Sheppard TD. Org. Biomol. Chem. 2011; 9: 1320
- 8 Hoefgen B, Decker M, Mohr P, Schramm AM, Rostom SA. F, El-Subbagh H, Schweikert PM, Rudolf DR, Kassack MU, Lehmann J. J. Med. Chem. 2006; 49: 760
- 9 Szawkało J, Czarnocki SJ, Zawadzka A, Wojtasiewicz K, Leniewski A, Maurin JK, Czarnockia Z, Drabowiczd J. Tetrahedron: Asymmetry 2007; 18: 406
- 10 Mohareb RM, Ahmed HH, Elmegeed GA, Abd-Elhalim MM, Shafic RW. Bioorg. Med. Chem. 2011; 19: 2966
- 11a Sabot C, Kumar KA, Meunier S, Mioskowski C. Tetrahedron Lett. 2007; 48: 3863
- 11b Geoghegan P, O’Leary P. Tetrahedron: Asymmetry 2010; 21: 867
- 12 CCDC976193 and CCDC976194 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.