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 2014; 46(19): 2551-2573
DOI: 10.1055/s-0034-1379023
DOI: 10.1055/s-0034-1379023
short review
Conhydrine: An Account of Isolation, Biological Perspectives and Synthesis
Further Information
Publication History
Received: 23 May 2014
Accepted after revision: 06 August 2014
Publication Date:
11 September 2014 (online)
Abstract
Conhydrine is a naturally occurring 2-substituted piperidine alkaloid from the plant Conium maculatum L that exists in four different forms and is known for its high toxicity. This article focuses on the synthesis of conhydrine as its medicinal applications are limited due to its high toxicity. The various asymmetric methods developed for the synthesis of conhydrine are classified based on the methodology: the chiral pool method, the chiral auixiliary method, and asymmetric catalysis. A brief overview of the complete synthetic coverage of conhydrine (1948–2014) in different isomeric forms is given.
1 Introduction
2 Isolation and Biological Perspectives
3 Synthesis
3.1 Chiral Pool Methods
3.2 From Achiral Starting Material
3.3 Chiral Auxiliary Mediated Synthesis
3.4 Catalysis Approach (Organo and Metal Catalysis)
4 Conclusion and Outlook
-
References
- 1a Hayashi Y, Rohde JJ, Corey EJ. J. Am. Chem. Soc. 1996; 118: 5502
- 1b Ager DJ, Prakash I, Schaad DR. Chem. Rev. 1996; 96: 835
- 1c Genow M, Dimitrov V, Ivanova V. Tetrahedron: Asymmetry 1997; 8: 3703
- 2 Casiraghi G, Zanardi F, Rassu G, Spanu P. Chem. Rev. 1995; 95: 1677
- 3a Buckingham J, Baggaley KH, Roberts AD, Szab LF. Dictionary of Alkaloids . CRC; Boca Raton: 2010. 2nd ed.
- 3b The Alkaloids: Chemistry and Biology . Vol. 54. Cordell GA. Academic Press; San Diego: 2000
- 3c Galliford CV, Scheidt KA. Angew. Chem. Int. Ed. 2007; 46: 8748
- 3d Pinder AR. Nat. Prod. Rep. 1992; 9: 17
- 3e Pinder AR. Nat. Prod. Rep. 1992; 9: 491
- 3f Rodrígez D, Wang CL. J, Wuonola MA. Org. Prep. Proced. Int. 1992; 583
- 3g Plunkett AO. Nat. Prod. Rep. 1994; 11: 581
- 3h Harrison T. Contemp. Org. Synth. 1995; 2: 209
- 4a Elbein AD, Molyneux RJ In Alkaloids: Chemical and Biological Perspectives . Vol. 5. Pelletier SW. Pergamon; Oxford: 1986: 1-54
- 4b Michael JP. Nat. Prod. Rep. 1997; 14: 619
- 5 Wertheim T. Justus Liebigs. Ann. Chem. 1856; 100: 328
- 6 Späth E, Adler E. Monatsh. Chem. 1933; 63: 127
- 7a Vetter J. Food. Chem. Toxicol. 2004; 42: 1373
- 7b Radulović N, Đorđević N, Denić M, Pinheiro MM. G, Fernandes PD, Boylan F. Food. Chem. Toxicol. 2012; 50: 274
- 8 Ahmad HM. T. Homoeopathy ‘Like Cures Like’ . Islam International Publications Ltd Islamabad; Tilford (UK): 2005
- 9 Galinovsky F, Mulley H. Monatsh. Chem. 1948; 79: 426
- 10 Ratovelomanana V, Royer J, Husson H.-P. Tetrahedron Lett. 1985; 26: 3803
- 11 Huang B, Yao X, Li C.-J. Adv. Synth. Catal. 2006; 348: 1528
- 12 Deshmukh SC, Roy A, Talukdar P. Org. Biomol. Chem. 2012; 10: 7536
- 13 Roy S, Sharma A, Mula S, Chattopadhyay S. Chem. Eur. J. 2009; 15: 1713
- 14 Gálvez JA, Díaz-de-Villegas MD, Badorrey R, López-Ram-de-Viú P. Org. Biomol. Chem. 2011; 9: 8155
- 15 Kamal A, Vangala SR, Reddy NV. S, Reddy VS. Tetrahedron: Asymmetry 2009; 20: 2589
- 16a Marton D, Stivanello D, Tagliavini G. J. Org. Chem. 1996; 61: 2731
- 16b Christian P, Jean LL. J. Org. Chem. 1985; 50: 910
- 16c Petrier C, Einhorn J, Luche JL. Tetrahedron Lett. 1985; 26: 1449
- 16d Cathy E, Jean LL. J. Organomet. Chem. 1987; 322: 177
- 17a Martinelli MJ, Nayyar NK, Moher ED, Dhokte UP, Pawlak JM, Vaidyanathan R. Org. Lett. 1999; 1: 447
- 17b Martinelli MJ, Vaidyanathan R, Pawlak JM, Nayyar NK, Dhokte UP, Doecke CW, Zollars LM. H, Moher ED, Van Khau V, Kosmrlj B. J. Am. Chem. Soc. 2002; 124: 3578
- 17c Martinelli MJ, Vaidyanathan R, Van Khau V. Tetrahedron Lett. 2000; 41: 3773
- 18 Venkataiah M, Fadnavis NW. Tetrahedron 2009; 65: 6950
- 19 Chattopadhyay A. J. Org. Chem. 1996; 61: 6104
- 20 Kamal A, Vangala SR. Tetrahedron 2011; 67: 1341
- 21 Kamal A, Reddy PV, Prabhakar S. Tetrahedron: Asymmetry 2009; 20: 1120
- 22 Jin T, Mu Y, Kim G.-W, Kim S.-S, Kim J.-S, Huh S.-I, Lee K.-Y, Joo J.-E, Ham W.-H. Asian J. Org. Chem. 2012; 1: 232
- 23 Ĉaplar V, Raza Z, Katalenić M, Žinić M. Croat. Chem. Acta 2003; 76: 23
- 24 Pandey SK, Kumar P. Tetrahedron Lett. 2005; 46: 4091
- 25a Gmieir P, Junge D, Kartner A. J. Org. Chem. 1994; 59: 6766
- 25b Oestreich M, Frohlich R, Hoppe D. Tetrahedron Lett. 1998; 39: 1745
- 26 Bhat C, Tilve SG. Tetrahedron 2013; 69: 10876
- 27 Guerreiro P, Ratovelomanana V.-V, Genêt J.-P. Chirality 2000; 12: 408
- 28 Chang M.-Y, Kung Y.-H, Chen S.-T. Tetrahedron 2006; 62: 10843
- 29 Srivastava AK, Das SK, Panda G. Tetrahedron 2009; 65: 5322
- 30 Agami C, Couty F, Rabasso N. Tetrahedron Lett. 2000; 41: 4113
- 31 Masaki Y, Imaeda T, Nagata K, Oda H, Ito A. Tetrahedron Lett. 1989; 30: 6395
- 32 Masaki Y, Serizawa Y, Nagata K, Oda H, Nagashima H, Kaji K. Tetrahedron Lett. 1986; 27: 231 ; and references cited there in
- 33 Dong GR, Hong S, Kim SI, Kim IS, Jung YH. Eur. J. Org. Chem. 2012; 4200
- 34a Kim IS, Zee OP, Jung YH. Org. Lett. 2006; 8: 4101
- 34b Kim IS, Li QR, Dong GR, Kim YC, Hong YG, Lee M, Chi K.-W, Oh JS, Jung YH. Eur. J. Org. Chem. 2010; 1569
- 35 Jamieson AG, Sutherland A. Org. Lett. 2007; 9: 1609
- 36 Reyes E, Ruiz N, Vicario JL, Badia D, Carrillo L. Synthesis 2011; 443
- 37 Bandini E, Corda G, D’Aurizio A, Panunzio M. Tetrahedron Lett. 2010; 51: 933
- 38 Reddipalli G, Venkataiah I, Fadnavis NW. Tetrahedron: Asymmetry 2011; 22: 1778
- 39 Rodríguiz D, Picó A, Moyano A. Tetrahedron Lett. 2008; 49: 6866
- 40 Kandula SR. V, Kumar P. Tetrahedron: Asymmetry 2005; 16: 3268
- 41 Nagata K, Toriizuka Y, Itoh T. Heterocycles 2005; 66: 107
- 42 Beng TK, Gawley RE. J. Am. Chem. Soc. 2010; 132: 12216
- 43 Comins DL, Williams AL. Tetrahedron Lett. 2000; 41: 2839
- 44 Comins DL, Salvador JM. Tetrahedron Lett. 1993; 34: 801
- 45 Voituriez A, Ferreira F, Chemla F. J. Org. Chem. 2007; 72: 5358
- 46 Louvel J, Chemla F, Demont E, Ferreira F, Pérez-Luna A, Voituriez A. Adv. Synth. Catal. 2011; 353: 2137
- 47 Voituriez A, Ferreira F, Pérez L.-A, Chemla F. Org. Lett. 2007; 9: 4705
- 48 Enders D, Nolte B, Raabe G, Runsink J. Tetrahedron: Asymmetry 2002; 13: 285
- 49 Lebrun S, Couture A, Deniau E, Grandclaudon P. Tetrahedron: Asymmetry 2008; 19: 1245
- 50 Shaikh TM, Sudalai A. Eur. J. Org. Chem. 2010; 3437
- 51 Liu S, Xie J.-H, Li W, Kong W.-L, Wang L.-X, Zhou Q.-L. Org. Lett. 2009; 11: 4994
- 52 Saikia PP, Baishya G, Goswami A, Barua NC. Tetrahedron Lett. 2008; 49: 6508
For reviews on piperidines and piperidine alkaloids see: