Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: Syntheses and applications

Amino Acids

Volumn 41, Issue 3, 2011, Pages 597-608

  Szakonyi, Zsolt ^a   Fülöp, Ferenc ^a  

^a UNIVERSITY OF SZEGED   (Hungary)

Author keywords

Asymmetric synthesis; Beta amino acid; Chiral; Chiral catalyst; Monoterpene

Indexed keywords

2 CHLOROPYRIMIDINE DERIVATIVE; 3 CARENE; APOPINANE BASED DERIVATIVE; BETA AMINO ACID; BETA AMINO ACID DERIVATIVE; BETA LACTAM; CHLOROSULFONYL ISOCYANATE; HETEROCYCLIC COMPOUND; ISOCYANIC ACID DERIVATIVE; NUCLEOPHILE; PROTEIN TYROSINE KINASE INHIBITOR; PYRIMIDINE DERIVATIVE; TERPENE; TERPENE DERIVATIVE; TERPINENE; TYROSINE KINASE AX1 INHIBITOR; UNCLASSIFIED DRUG;

ANTICONVULSANT ACTIVITY; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CONFERENCE PAPER; CYCLOADDITION; HYDROLYSIS; ISOMERIZATION; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

AMINO ACIDS; BETA-LACTAMS; CATALYSIS; ESTERS; MONOTERPENES; PEPTIDES; STEREOISOMERISM; TERPENES; THIOUREA;

EID: 80052330024     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-0891-5     Document Type: Conference Paper

References (46)

1. Ager D (ed) (2006) Handbook of chiral chemicals. Taylor and Francis, Boca Raton
2. B Alcaide P Almendros C Aragoncillo 2007 β-Lactams: versatile building blocks for the stereoselective synthesis of non-β-lactam products Chem Rev 107 4437 4592 17649981 10.1021/cr0307300 1:CAS:528:DC%2BD2sXotFeitrs%3D (Pubitemid 350225859)
3. L Atodiresei I Schiffers C Bolm 2007 Stereoselective anhydride openings Chem Rev 107 5683 5712 18072807 10.1021/cr068369f 1:CAS:528:DC%2BD2sXhsVSqsL3J
4. Bolm C, Schiffers I, Dinter CL, Defrere L, Gerlach A, Raabe G (2001) Efficient asymmetric synthesis of unnatural β-amino acids. Synthesis-Stuttgart 1719-1730 (Pubitemid 32831673)
5. Y Chen P McDaid L Deng 2003 Asymmetric alcoholysis of cyclic anhydrides Chem Rev 103 2965 2984 12914488 10.1021/cr020037x 1:CAS:528:DC%2BD3sXlslKiurk%3D
6. C Cimarelli G Palmieri 1996 Stereoselective reduction of enantiopure β-enamino esters by hydride: a convenient synthesis of both enantiopure β-amino esters J Org Chem 61 5557 5563 10.1021/jo960107y 1:CAS:528:DyaK28XksVSlu7s%3D (Pubitemid 26272779)
7. SG Davies AD Smith PD Price 2005 The conjugate addition of enantiomerically pure lithium amides as homochiral ammonia equivalents: scope, limitations and synthetic applications Tetrahedron Asymmetr 16 2833 2891 10.1016/j.tetasy.2005.08.006 1:CAS:528:DC%2BD2MXpvVSqs78%3D (Pubitemid 41253491)
8. Dhar DN, Dhar P (eds) (2002) The chemistry of chlorosulfonyl isocyanate. World Scientific Publishing, Singapore
9. Enders D, Wiedemann J, Bettray W (1995) Diastereoselective and enantioselective synthesis of trans-2-amino-cycloalkane-1-carboxylic acids via intramolecular tandem Michael-addition alpha-alkylation using TMS-SAMP as chiral equivalent of ammonia. Synlett 369-371
10. C Fernandes E Pereira S Faure DJ Aitken 2009 Expedient preparation of all isomers of 2-aminocyclobutanecarboxylic acid in enantiomerically pure form J Org Chem 74 3217 3220 19284796 10.1021/jo900175p 1:CAS:528:DC%2BD1MXjtlSisLY%3D
11. F Forró F Fülöp 2004 Direct and indirect enzymatic methods for the preparation of enantiopure cyclic β-amino acids and derivatives from β-lactams Mini Rev Org Chem 1 93 102 10.2174/ 1570193043488908
12. F Fülöp 2001 The chemistry of 2-aminocycloalkanecarboxylic acids Chem Rev 101 2181 2204 11710244 10.1021/cr000456z (Pubitemid 35377795)
13. Fülöp F, Szakonyi Z (2008) Chiral cyclic β-amino acids and their derivatives, pharmaceutical compositions containing them and the use of such compounds. PCT: WO 2008/059299 A1
14. Fülöp F, Martinek TA, Tóth GK (2006) Application of alicyclic β-amino acids in peptide chemistry. Chem Soc Rev 35:323-334 and references cited therein
15. Fülöp F, Szakonyi Z, Pallai PV (2010) PCT: WO 2010070365 A1
16. S Gyónfalvi Z Szakonyi F Fülöp 2003 Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-3-carene Tetrahedron Asymmetr 14 3965 3972 10.1016/j.tetasy.2003.10.001 (Pubitemid 37500893)
17. Z Hameršak M Roje A Avdagić V Šunjic 2007 Quinine-mediated parallel kinetic resolution of racemic cyclic anhydride: stereoselective synthesis, relative and absolute configuration of novel alicyclic β-amino acids Tetrahedron Asymmetr 18 635 644 10.1016/j.tetasy.2007.02.019 (Pubitemid 46507755)
18. Hetényi A, Szakonyi Z, Mándity MI, Szolnoki É, Tóth GK, Martinek TA, Fülöp F (2009) Sculpting the β-peptide foldamer H12 helix via a designed side chain shape. Chem Commun 177-179
19. Juaristi E, Soloshonok VA (eds) (2005) Enantioselective synthesis of β-amino acids. Wiley-Interscience, New York
20. A Kamal PB Sattur 1987 Chlorosulfonyl isocyanate: a novel reagent for the synthesis of heterocycles Heterocycles 26 1051 1076 10.3987/R-1987-04-1051 1:CAS:528:DyaL2sXmtlKmsbY%3D
21. EA Koneva KP Volcho YV Gatilov DV Korchagina GE Salnikov NF Salakhutdinov 2008 Synthesis of derivatives of the optically active β-amino acids from (+)-car-2-ene Helv Chim Acta 91 1849 1856 10.1002/hlca.200890197 1:CAS:528:DC%2BD1cXhsVWktLfN
22. EA Koneva KP Volcho DV Korchagina NI Komarova AI Kochnev NF Salakhutdinov AG Tolstikov 2008 New chiral Schiff bases derived from (+)- and (-)-α-pinenes in the metal complex catalyzed asymmetric oxidation of sulfides Russian Chem Bull 57 108 117 10.1007/s11172-008-0017-8 1:CAS:528:DC%2BD1MXlvFKmsQ%3D%3D
23. EA Koneva TM Khomenko SY Kurbakova NI Komarova DV Korchagina KP Volcho NF Salakhutdinov AG Tolstikov GA Tolstikov 2008 Synthesis of optically active omeprazole by catalysis with vanadyl complexes with chiral Schiff bases Russ Chem Bull Int Ed 57 1680 1685 10.1007/s11172-008-0221-6 1:CAS:528: DC%2BD1MXps1yqs74%3D
24. Koneva EA, Volcho KP, Korchagina DV, Salakhutdinov NF, Tolstikov AG (2009) Synthesis of new chiral schiff bases from (+)-3-carene and their use in asymmetric oxidation of sulfides catalyzed by metal complexes. Russ J Org Chem 45:815-824
25. A Kuhl MG Hahn M Dumić J Mittendorf 2005 Alicyclic β-amino acids in medicinal chemistry - review article Amino Acids 29 89 100 15986181 10.1007/s00726-005-0212-y 1:CAS:528:DC%2BD2MXos1eltb8%3D (Pubitemid 41191390)
26. SM Lait DA Rankic BA Keay 2007 1, 3-Aminoalcohols and their derivatives in asymmetric organic synthesis Chem Rev 107 767 796 17319729 10.1021/cr050065q 1:CAS:528:DC%2BD2sXitVKns78%3D (Pubitemid 46502371)
27. FZ Makaev AV Malkov 2006 Use of monoterpenes, 3-carene and 2-carene, as synthons in the stereoselective synthesis of 2, 2-dimethyl-1, 3-disubstituted cyclopropanes Tetrahedron Asymmetr 62 9 29 (Pubitemid 41740958)
28. FZ Makaev LA Vlad LP Bets ST Malinovskii KN Gavrilov M Gdanets 2010 Addition products of chlorosulfonyl isocyanate to (+)-3-carene and α-pinene enantiomers Chem Nat Prod 46 528 533 1:CAS:528:DC%2BC3cXhtVKgtrjI
29. AG Moglioni E García-Expósito GP Aguado T Parella V Branchadell GY Moltrasio RM Ortuño 2000 Divergent routes to chiral cyclobutane synthons from (-)-α-pinene and their use in the stereoselective synthesis of dehydro amino acids J Org Chem 65 3934 3940 10866610 10.1021/jo991773c 1:CAS:528:DC%2BD3cXjslGlurk%3D (Pubitemid 32063394)
30. AG Moglioni E Muray JA Castillo Á Álvarez-Larena GY Moltrasio V Branchadell RM Ortuño 2002 Reaction between N-alkylhydroxylamines and chiral enoate esters: More experimental evidence for a cycloaddition-like process, a rationale based on DFT theoretical calculations, and stereoselective synthesis of new enantiopure β-amino acids J Org Chem 67 2402 2410 11950280 10.1021/jo0159082 1:CAS:528:DC%2BD38XhvFOnsbk%3D (Pubitemid 34298849)
31. M Ordoñez C Cativiela 2007 Stereoselective synthesis of γ-amino acids Tetrahedron Asymmetr 18 3 99 10.1016/j.tetasy.2006.12.001 (Pubitemid 46205308)
32. JK Rasmussen A Hassner 1976 Recent developments in the synthetic uses of chlorosulfonyl isocyanate Chem Rev 76 389 408 10.1021/cr60301a004 1:CAS:528:DyaE28Xks1ahsrg%3D
33. T Sasaki S Eguchi H Yamada 1973 Reactions of isoprenoids. XVIII. Reactions of chlorosulfonyl isocyanate with bicyclic monoterpene olefins. Novel isomerization of 1-chlorosulfonyl-2-azetidinone J Org Chem 38 679 686 10.1021/jo00944a014 1:CAS:528:DyaE3sXpslyiug%3D%3D
34. M Sathe R Ghorpade MP Kaushik 2006 Highly efficient methanolysis of bicyclic β-lactams to β-amino ester using silica chloride Chem Lett 35 1004 1005 10.1246/cl.2006.1004 1:CAS:528:DC%2BD28XhtVCksrnJ (Pubitemid 44859887)
35. DF Shellhamer KJ Davenport DM Hassler KR Hickle JJ Thorpe DJ Vandenbroek VL Heasley JA Boatz AL Reingold CE Moore 2010 Reaction of chlorosulfonyl isocyanate with fluorosubstituted alkenes: evidence of a concerted pathway J Org Chem 75 22 7913 7916 10.1021/jo101240s 1:CAS:528:DC%2BC3cXhtlWmtL7K
36. Singh R, Ding P, Holland S, Goff D (2008) Pinane-substituted pyrimidinediamine derivatives useful as Axl inhibitors. PCT: WO 2008/045978 A1
37. Z Szakonyi F Fülöp 2003 Mild and efficient ring opening of monoterpene-fused β-lactam enantiomers. Synthesis of novel β-amino acid derivatives Arkivoc 14 225 232 (Pubitemid 38957191)
38. Z Szakonyi TA Martinek A Hetényi F Fülöp 2000 Synthesis and transformations of enantiomeric 1, 2-disubstituted monoterpene derivatives Tetrahedron Asymmetr 11 4571 4579 10.1016/S0957-4166(00)00435-3 1:CAS:528:DC%2BD3MXjt1entw%3D%3D (Pubitemid 32123672)
39. Z Szakonyi Á Balázs TA Martinek F Fülöp 2006 Enantioselective addition of diethylzinc to aldehydes catalyzed by γ-amino alcohols derived from (+)- and (-)-α-pinene Tetrahedron Asymmetr 17 199 204 10.1016/j.tetasy.2005.12.011 1:CAS:528:DC%2BD28Xht1ymtrg%3D (Pubitemid 43226628)
40. Z Szakonyi TA Martinek R Sillanpää F Fülöp 2007 Regio- and stereoselective synthesis of the enantiomers of monoterpene-based β-amino acid derivatives Tetrahedron Asymmetr 18 2442 2447 10.1016/j.tetasy.2007.09.028 1:CAS:528:DC%2BD2sXht1OqsrjK (Pubitemid 350018994)
41. Z Szakonyi TA Martinek R Sillanpää F Fülöp 2008 Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives Tetrahedron Asymmetr 19 2296 2303 10.1016/j.tetasy.2008.09.026 1:CAS:528:DC%2BD1cXhtlWksLnI
42. Z Szakonyi R Sillanpää F Fülöp 2010 Synthesis of conformationally constrained tricyclic beta-lactam enantiomers through Ugi four-center three-component reactions of a monoterpene-based β-amino acid Mol Div 14 59 65 10.1007/s11030-009-9143-y 1:CAS:528:DC%2BC3cXhslOjs7s%3D
43. Z Szakonyi Á Balázs TA Martinek F Fülöp 2010 Stereoselective synthesis of pinane-based β- and γ-amino acids via conjugate addition of lithium amides and nitromethane Tetrahedron Asymmetr 21 2498 2504 10.1016/j.tetasy.2010.09.009 1:CAS:528:DC%2BC3cXhsVKjt7zI
44. TG Tolstikova EA Morozova AV Pavlova AV Bolkunov MP Dolgikh EA Koneva KP Volcho NF Salakhutdinov GA Tolstikov 2008 Derivatives of pinane amino acids as new anticonvulsants Doklady Chem 422 248 250 10.1134/S0012500808100029 1:CAS:528:DC%2BD1cXht1Kjt7fP
45. E Torres C Acosta-Silva F Rúa Á Álvarez-Larena T Parella V Branchadell RM Ortuño 2009 Synthesis and structural study of novel dimethylcyclobutyl β-peptides Tetrahedron 65 5669 5675 10.1016/j.tet.2009.05.039 1:CAS:528:DC%2BD1MXntlSmsrY%3D
46. A Trabocchi D Scarpi A Guarna 2008 Structural diversity of bicyclic amino acids Amino Acids 34 1 24 17701095 10.1007/s00726-007-0588-y 1:CAS:528:DC%2BD1cXlt1ClsA%3D%3D