Asymmetric Synthesis of Pipecolic Acid and Derivatives

Abstract

The nonproteinogenic α-amino acid, l-pipecolic acid and its derivatives are components of a wide range of pharmacologically active compounds. The significant biological activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This review highlights these key methods as well as the application of these compounds for the preparation of enzyme inhibitors, conformationally restricted building blocks and peptidomimetics.

1 Introduction

2 Chiral Pool Approaches

2.1 From Amino Acids

2.2 From Carbohydrates

3 Asymmetric Reactions

3.1 Auxiliary-Based Approaches

3.2 Catalytic Asymmetric Methods

4 Chemoenzymatic Methods

4.1 Enzymatic Kinetic Resolution

4.2 Miscellaneous Enzymatic Methods

5 Synthesis of Pipecolic Acid Derivatives for Biological Applications

5.1 Synthesis of Novel Medicinal Agents

5.2 Synthesis of Conformationally Restricted Building Blocks (Peptide and Nucleic Acid Mimics)

6 Conclusions

Key words

amino acids - heterocycles - piperidines - asymmetric synthesis - asymmetric catalysis

• References

• 1 He M. J. Ind. Microbiol. Biotechnol. 2006; 33: 401
• 2a Zacharius RM, Thompson JF, Steward FC. J. Am. Chem. Soc. 1952; 74: 2949
• 2b Bernasconi R, Jones RS. G, Bittiger H, Olpe HR, Heid J, Martin P, Klein M, Loo P, Braunwalder A, Schmutz M. J. Neural Transm. 1986; 67: 175
• 3 Gutiérrez MC, Delgado-Coello BA. Neurochem. Res. 1989; 14: 405
• 4 Pacella E, Collini S, Pacella F, Piraino DC, Santamaria V, De Blasi RA. Eur. Rev. Med. Pharmacol. Sci. 2010; 14: 539
• 5a Swindells DC, White PS, Findlay JA. Can. J. Chem. 1978; 56: 2491
• 5b Smith III AB, Hale KJ, Laakso LM, Chen K, Riéra A. Tetrahedron Lett. 1989; 30: 6963
• 5c Smith III AB, Condon SM, McCauley JA, Leazer JL. Jr, Leahy JW, Maleczka RE. Jr. J. Am. Chem. Soc. 1997; 119: 962
• 5d Smith III AB, Adams CM. Acc. Chem. Res. 2004; 37: 365
• 6a Tanaka H, Kuroda A, Marusawa H, Hatanaka H, Kino T, Goto T, Hashimoto M, Taga T. J. Am. Chem. Soc. 1987; 109: 5031
• 6b Romo D, Meyer SD, Johnson DD, Schreiber SL. J. Am. Chem. Soc. 1993; 115: 7906
• 6c Ireland RE, Gleason JL, Gregnas LD, Highsmith TK. J. Org. Chem. 1996; 61: 6856
• 7 Boger DL, Chen J.-H, Saionz KW. J. Am. Chem. Soc. 1996; 118: 1629
• 8a Suzuki K, Sato T, Morioka M, Nagai K, Abe K, Yamaguchi H, Sato T, Takeshi O, Susaki K. J. Antibiot. 1991; 44: 479
• 8b Scott JD, Tippie TN, Williams RM. Tetrahedron Lett. 1998; 39: 3659
• 9 Letavic MA, Axt MZ, Barberia JT, Carty TJ, Danley DE, Geoghegan KF, Halim NS, Hoth LR, Kamath AV, Laird ER, Lopresti-Morrow LL, McClure KF, Mitchell PG, Natarajan V, Noe MC, Pandit J, Reeves L, Schulte GK, Snow SL, Sweeney FJ, Tan DH, Yu CH. Bioorg. Med. Chem. Lett. 2002; 12: 1387
• 10a Anderson PC, Soucy F, Yoakim C, Lavallee P, Beaulieu PL. US Patent 5614533 A 19970325, 1997
• 10b Lamarre D, Croteau G, Wardrop E, Bourgon L, Thibeault D, Clouette C, Vaillancourt M, Cohen E, Pargellis C, Yoakim C, Anderson PC. Antimicrob. Agents Chemother. 1997; 41: 965
• 11 Kadouri-Puchot C, Comesse S. Amino Acids 2005; 29: 101
• 12 Chang M.-Y, Kung Y.-H, Wu T.-C. Heterocycles 2006; 68: 2365
• 13 Chattopadhyay SK, Roy SP, Saha T. Synthesis 2011; 2664
• 14 Fowler LS, Thomas LH, Ellis D, Sutherland A. Chem. Commun. 2011; 47: 6569
• 15 Botman PN. M, Dommerholt FJ, de Gelder R, Broxterman QB, Schoemaker HE, Rutjes FP. J. T, Blaauw RH. Org. Lett. 2004; 6: 4941
• 16 Liang N, Datta A. J. Org. Chem. 2005; 70: 10182
• 17 Hanessian S, Riber L, Marin J. Synlett 2009; 71
• 18 Cordero FM, Fantini P, Brandi A. Synlett 2006; 3251
• 19 Cariou CA. M, Kariuki BM, Snaith JS. Org. Biomol. Chem. 2008; 6: 3337
• 20 Shirude PS, Kumar VA, Ganesh KN. Tetrahedron 2004; 60: 9845
• 21 Le Maux P, Nicolas I, Chevance S, Simonneaux G. Tetrahedron 2010; 66: 4462
• 22 Jung J.-C, Avery MA. Tetrahedron: Asymmetry 2006; 17: 2479
• 23 Mykhailiuk PK, Shishkina SV, Shishkin OV, Zaporozhets OA, Komarov IV. Tetrahedron 2011; 67: 3091
• 24 Chattopadhyay SK, Biswas T, Biswas T. Tetrahedron Lett. 2008; 49: 1365
• 25 van den Broek SA. M. W, Rensen PG. W, van Delft FL, Rutjes FP. J. T. Eur. J. Org. Chem. 2010; 5906
• 26 Chattopadhyay A, Mamdapur VR. J. Org. Chem. 1995; 60: 585
• 27 Alcaide B, Almendros P, Luna A, del Campo TM. J. Org. Chem. 2008; 73: 1635
• 28 Pawar VU, Chavan ST, Sabharwal SG, Shinde VS. Bioorg. Med. Chem. Lett. 2010; 18: 7799
• 29 Tronchet JM. J, Gentile B, Ojha-Poncet J, Moret G, Schwarzenbach D, Barblat-Rey F, Tronchet J. Carbohydr. Res. 1977; 59: 87
• 30 Kumar PS, Baskaran S. Tetrahedron Lett. 2009; 50: 3489
• 31 Chavan SP, Harale KR, Dumare NB, Kalkote UR. Tetrahedron: Asymmetry 2011; 22: 587
• 32 Rhee JU, Bliss BI, Rajanbabu TV. J. Am. Chem. Soc. 2003; 125: 1492
• 33 Timmer MS. M, Risseeuw MD. P, Verdoes M, Filippov DV, Plaisier JR, van der Marel GA, Overkleeft HS, van Boom JH. Tetrahedron: Asymmetry 2005; 16: 177
• 34 Merino P, Mannucci V, Tejero T. Eur. J. Org. Chem. 2008; 3943
• 35a Kim DC, Yoo KH, Kim DJ, Chung BY, Park SW. Tetrahedron Lett. 1999; 40: 4825
• 35b Davis BG, Maughan MA. T, Chapman TM, Villard R, Courtney S. Org. Lett. 2002; 4: 103
• 35c Valentine DH. Jr, Hillhouse JH. Synthesis 2003; 317
• 36 Lemire A, Charette AB. J. Org. Chem. 2010; 75: 2077
• 37 Carlsen PH. J, Katsuki T, Martin VS, Sharpless KB. J. Org. Chem. 1981; 46: 3936
• 38 Hou D.-R, Hung S.-Y, Hu C.-C. Tetrahedron: Asymmetry 2005; 16: 3858
• 39 Calosso M, Wagner M, Gendrineau T, Petit M, Kadouri-Puchot C, Dechoux L. Lett. Org. Chem. 2007; 4: 4
• 40 Tsimilaza A, Tite T, Boutefnouchet S, Lallemand M.-C, Tillequin F, Husson H.-P. Tetrahedron: Asymmetry 2007; 18: 1585
• 41 Jatoi WB, Bariau A, Esparcieux C, Figueredo G, Troin Y, Canet J.-L. Synlett 2008; 1305
• 42 Sun C.-S, Lin Y.-S, Hou D.-R. J. Org. Chem. 2008; 73: 6877
• 43 Fustero S, Mateu N, Simón-Fuentes A, Aceña JL. Org. Lett. 2010; 12: 3014
• 44 Titanyuk ID, Beletskaya IP. Russ. J. Org. Chem. 2010; 46: 1277
• 45 Cordero FM, Bonollo S, Machetti F, Brandi A. Eur. J. Org. Chem. 2006; 3235
• 46 Maison W. Eur. J. Org. Chem. 2007; 2276
• 47 Caballero E, Figueroa J, Puebla P, Peláez R, Tomé F, Medarde M. Eur. J. Org. Chem. 2008; 4004
• 48 Ferraboschi P, De Mieri M, Grisenti P, Lotz M, Nettekoven U. Tetrahedron: Asymmetry 2011; 22: 1626
• 49 Fadel A, Lahrache N. J. Org. Chem. 2007; 72: 1780
• 50 Acherki H, Alvarez-Ibarra C, Guzmán-Fernández S, Quiroga-Feijóo ML. Tetrahedron: Asymmetry 2004; 15: 693
• 51 González-Gómez JC, Foubelo F, Yus M. Synlett 2008; 2777
• 52a Ohbayashi T, Mitsunaga S, Satoh T. Tetrahedron Lett. 2007; 48: 7829
• 52b Mitsunaga S, Ohbayashi T, Sugiyama S, Saitou T, Tadokoro M, Satoh T. Tetrahedron: Asymmetry 2009; 20: 1697
• 53 Wang B, Liu R.-H. Eur. J. Org. Chem. 2009; 2845
• 54 Markandeya N, Shankaraiah N, Reddy CS, Santos LS, Kamal A. Tetrahedron: Asymmetry 2010; 21: 2625
• 55 Hung K.-y, Harris PW. R, Brimble MA. J. Org. Chem. 2010; 75: 8728
• 56 Chang M.-Y, Lee M.-F, Lee N.-C, Huang Y.-P, Lin C.-H. Tetrahedron Lett. 2011; 52: 588
• 57 Fitzi R, Seebach D. Tetrahedron 1988; 44: 5277
• 58 Purkayastha N, Shendage DM, Fröhlich R, Haufe G. J. Org. Chem. 2010; 75: 222
• 59 Purkayastha N, Haufe G. Synlett 2010; 1501
• 60a Alegret C, Santacana F, Riera A. J. Org. Chem. 2007; 72: 7688
• 60b Alegret C, Ginesta X, Riera A. Eur. J. Org. Chem. 2008; 1789
• 61a Hekking KF. W, Lefort L, de Vries AH. M, van Delft FL, Schoemaker HE, de Vries JG, Rutjes FP. J. T. Adv. Synth. Catal. 2008; 350: 85
• 61b Hekking KF. W, Waalboer DC. J, Moelands MA. H, van Delft FL, Rutjes FP. J. T. Adv. Synth. Catal. 2008; 350: 95
• 62a Seitz T, Baudoux J, Bekolo H, Cahard D, Plaquevent J.-C, Lasne M.-C, Rouden J. Tetrahedron 2006; 62: 6155
• 62b Martin J, Plaquevent J.-C, Maddaluno J, Rouden J, Lasne M.-C. Eur. J. Org. Chem. 2009; 5414
• 63 Kano T, Kumano T, Sakamoto R, Maruoka K. Nat. Chem. Sci. 2010; 1: 499
• 64 Kalch D, De Rycke N, Moreau X, Greck C. Tetrahedron Lett. 2009; 50: 492
• 65 Beng TK, Gawley RE. J. Am. Chem. Soc. 2010; 132: 12216
• 66 Kelly NM, Sutherland A, Willis CL. Nat. Prod. Rep. 1997; 14: 205
• 67 Winkler M, Meischler D, Klempier N. Adv. Synth. Catal. 2007; 349: 1475
• 68 Wuggenig F, Schweifer A, Mereiter K, Hammerschmidt F. Eur. J. Org. Chem. 2011; 1870
• 69 Watanabe LA, Haranaka S, Jose B, Yoshida M, Kato T, Moriguchi M, Soda K, Nishino N. Tetrahedron: Asymmetry 2005; 16: 903
• 70a Ohara C, Takahashi R, Miyagawa T, Yoshimura Y, Kato A, Adachi I, Takahata H. Bioorg. Med. Chem. Lett. 2008; 18: 1810
• 70b Yoshimura Y, Ohara C, Imahori T, Saito Y, Kato A, Miyauchi S, Adachi I, Takahata H. Bioorg. Med. Chem. 2008; 16: 8273
• 71 Bartali L, Casini A, Guarna A, Occhiato EG, Scarpi D. Eur. J. Org. Chem. 2010; 5831
• 72 Occhiato EG, Casini A, Guarna A, Scarpi D. Eur. J. Org. Chem. 2011; 6544
• 73 Sonke T, Kaptein B, Schoemaker HS In Amino Acids, Peptides and Proteins in Organic Chemistry. Vol. 1. Hughes AB. Wiley-VCH; Weinheim: 2009: 79
• 74 Muramatsu H, Mihara H, Yasuda M, Ueda M, Kurihara T, Easki N. Biosci. Biotechnol. Biochem. 2006; 70: 2296
• 75 Yasuda M, Ueda M, Muramatsu H, Mihara H, Easki N. Tetrahedron: Asymmetry 2006; 17: 1775
• 76 Ni Y, Li C.-X, Wang L.-J, Zhang J, Xu J.-H. Org. Biomol. Chem. 2011; 9: 5463
• 77 Occhiato EG, Scarpi D, Guarna A. Eur. J. Org. Chem. 2008; 524
• 78 Occhiato EG, Scarpi D, Guarna A, Tabasso S, Deagostino A, Prandi C. Synthesis 2009; 3611
• 79 Klein C, Hüttel W. Adv. Synth. Catal. 2011; 353: 1375
• 80 Ornstein PL, Schoepp DD, Arnold MB, Leander JD, Lodge D, Paschal JW, Elzey T. J. Med. Chem. 1991; 34: 90
• 81a Lenda F, Guenoun F, Tazi B, Larbi NB, Martinez J, Lamaty F. Tetrahedron Lett. 2004; 45: 8905
• 81b Lenda F, Guenoun F, Tazi B, Larbi NB, Allouchi H, Martinez J, Lamaty F. Eur. J. Org. Chem. 2005; 326
• 82 Bulusu MA. R. C, Waldstätten P, Tricotet T, Rochais C, Steck A, Bacher M. Tetrahedron Lett. 2004; 45: 5833
• 83 Hanessian S, Gauchet C, Charron G, Marin J, Nakache P. J. Org. Chem. 2006; 71: 2760
• 84 Machetti F, Cordero FM, De Sarlo F, Papini AM, Alcaro MC, Brandi A. Eur. J. Org. Chem. 2004; 2928
• 85 Lonkar PS, Kumar VA. J. Org. Chem. 2005; 70: 6956
• 86a Le Corre L, Dhimane H. Tetrahedron Lett. 2005; 46: 7495
• 86b Le Corre L, Kizirian J.-C, Levraud C, Boucher J.-L, Bonnet V, Dhimane H. Org. Biomol. Chem. 2008; 6: 3388
• 87 Gupta S, Das BC, Schafmeister CE. Org. Lett. 2005; 7: 2861
• 88 Ellis GL, O’Neil IA, Ramos VE, Kalindjian SB, Chorlton AP, Tapolczay DJ. Tetrahedron Lett. 2007; 48: 1687
• 89 Somu RV, Johnson RL. J. Org. Chem. 2005; 70: 5954
• 90 Casabona D, Cativiela C. Tetrahedron 2006; 62: 10000
• 91 Radchenko DS, Kopylova N, Grygorenko OO, Komarov IV. J. Org. Chem. 2009; 74: 5541