Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2- carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral β-nitroacrylate

Chirality

Volumn 23, Issue 3, 2011, Pages 245-249

  Calmes, Monique ^a   Escale, Françoise ^a   Didierjean, Claude ^b   Martinez, Jean ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b Nancy University CNRS   (France)

Author keywords

asymmetric synthesis; bicyclic amino acids; bicyclic 1,3 amino alcohol; chiral nitroacrylate; Diels Alder reactions

Indexed keywords

1,3 CYCLOHEXADIENE; 3 (HYDROXYMETHYL) 2 AMINOBICYCLIC[2,2,2]OCTANIC ACID TRIFLUOROACETIC ACID; 3 TERT BUTOXYCARBONYLAMINOBICYCLO[2.2.2]OCTANE 2 CARBOXYLIC ACID; [ N (4 CARBOXYPHENYL) 4,4 DIMETHYL 2 OXOPYRROLIDINOXOPYRROLIDIN 3 YL] 1 (3 TERTBUTOXYCARBONYLAMINOBICYCLO[2.2.2]OCTANE 2 CARBOXYLATE; ACRYLIC ACID DERIVATIVE; ALICYCLIC HYDROCARBON; AMINOALCOHOL; BENZOIC ACID; BETA NITROACRYLATE; BICYCLO[2.2.2]OCTANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; N BOC 3 (HYDROXYMETHYL) 2 AMINOBICYCLIC[2,2,2]OCTANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; PRIORITY JOURNAL; SYNTHESIS;

AMINO ACIDS, CYCLIC; AMINO ALCOHOLS; BICYCLO COMPOUNDS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXENES; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 79951484832     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20906     Document Type: Article

References (42)

1. Ono N,. The nitro group in organic synthesis. New-York: Wiley-VCH; 2001.
2. Bunnage ME, Ganesh T, Masesane IB, Orton D, Stell PG,. Asymmetric synthesis of the putative structure of (-)-oryzoxymycin. Org Lett 2003; 5: 239-242. (Pubitemid 37141159)
3. Masesane IB, Stell PG,. Stereoselective routes to polyhydroxylated cyclohexyl-β-amino acids. Synlett 2003; 5: 735-737. (Pubitemid 36469604)
4. Caputo F, Clerici F, Gelmi ML, Nava D, Pellegrino S,. Uncatalyzed solventless Diels-Alder reaction of 2-amino-3-nitroacrylate: synthesis of new epimeric 2-amino-3-nitro-norbornene- and norbornane-2-carboxylic acids. Tetrahedron 2006; 62: 1288-1293.
5. Masesane IB, Batsanov AS, Howard JA, Mondal K, Steel PG,. The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid. Beilstein J Org Chem 2006; 2: 1-6.
6. Clive DLJ, Bo Y, Selvakumar N,. Synthesis and X-ray crystal structure of (-)-calicheamicinone. Tetrahedron 1999; 55: 3277-3290. (Pubitemid 29125386)
7. Calmès M, Escale F, Didierjean C, Cazals G, Martinez J,. Asymmetric Diels-Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acids preparation. Tetrahedron: Asymmetry 2007; 18: 2491-2496. (Pubitemid 350019631)
8. Juaristi E,. Enantioselective synthesis of β-Aminoacids. New-York: Wiley-VLH; 1997. p 1-66.
9. Rowinsky EK, Donehower RC,. The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics. Pharmacol Ther 1991; 52: 35-41.
10. Guenard D, Gueritte-Voegelein F, Potier P,. Taxol and taxotere: discovery, chemistry, and structure-activity relationships. Acc Chem Res 1993; 26: 160-168.
11. Ojima I, Lin S, Wang T,. Recent advances in the medicinal chemistry of taxoids with novel beta-amino acid side chains. Curr Med Chem 1999; 6: 927-954. (Pubitemid 29455182)
12. 2-Amino acids-syntheses, occurrence in natural products and components of β-peptides. Biopolymers (Peptide Science) 2004; 76: 206-243. (Pubitemid 38724851)
13. Kuhl A, Hahn G, Dumic M, Mittendorf J,. Alicyclic β-amino acids in medicinal chemistry. Amino Acids 2005; 29: 89-100. (Pubitemid 41191390)
14. Gellman SH,. Foldamers: A Manifesto. Acc Chem Res 1998; 31: 173-180. (Pubitemid 128474551)
15. Cheng PG, Gellman SH, DeGrado WF,. β-Peptides: from structure to function. Chem Rev 2001; 101: 3219-3232.
16. Sukopp M, Schwab R, Marinelli L, Biron E, Heller M, Varkondi E, Pap A, Novellino E, Kéri G, Kessler H,. Structure-activity relationship studies optimizing the antiproliferative activity of novel cyclic somatostatin analogues containing a restrained cyclic β-amino acid. J Med Chem 2005; 48: 2916-2926. (Pubitemid 40548105)
17. Fülöp F, Martinek TA, Toth GK,. Application of alicyclic β-aminoacids in peptide chemistry. Chem Soc Rev 2006; 35: 323-334. (Pubitemid 43475199)
18. Fülöp F,. The chemistry of 2-aminocyclohexanecarboxylic acids. Chem Rev 2001; 101: 2181-2204.
19. Hayashi Y, Rohde JJ, Corey EJ,. A novel chiral super-Lewis acidic catalyst for enantioselective synthesis. J Am Chem Soc 1996; 118: 5502-5503. (Pubitemid 26201017)
20. Li X, Yeung C-H, Chan ASC, Yang T-K,. New 1,3-amino alcohols derived from ketopinic acids and their application in catalytic enantioselective reduction of prochiral ketones. Tetrahedron: Asymmetry 1999; 10: 759-763. (Pubitemid 29179851)
21. Balazs A, Szakonyi Z, Fülöp F,. Synthesis of alicyclic N-substituted 1,3-amino alcohol via 1,3-oxazines. J Heterocyclic Chem 2007; 44: 403-406. (Pubitemid 350205240)
22. Fülöp F, Szakonyi Z, Bernath G, Sohar P,. Saturated heterocycles: synthesis of 2,4-dioxo and 4-oxo-2-thioxo derivatives of octahydrocyclopenta[d]pyrimidines. J Heterocyclic Chem 1997; 34: 1211-1214.
23. Kivelä H, Klika KD, Szabo A, Stajer G, Pihlaja K,. Structures of saturated 5H-pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones prepared from 4-oxopentanoic acid and cyclic amino alcohols. Eur J Org Chem 2003; 1879-1886.
24. Kivelä H, Zalan Z, Tahtinen P, Sillanpää R, Fülöp F, Pihlaja K,. Synthesis and conformational analysis of saturated 3,1,2-benzoxazaphosphinine 2-oxides. Eur J Org Chem 2005; 1189-1200. (Pubitemid 40444975)
25. Roberts JD, Moreland WT, Frazer W,. Synthesis of some 4-substituted bicyclo[2.2.2]octane carboxylic acids. J Am Chem Soc 1953; 75: 637-640.
26. Wynn CM, Vaughan WR,. Stereochemistry of pyrrolidine addition to bicyclo[2.2.2]oct-2-ene -2-carbonitrile. J Org Chem 1968; 33: 2371-2374.
27. Clarke C, Fleming I, Fortunak JM, Gallagher PT, Honan MC, Mann A, Nubling CO, Raithby PR, Wolff JJ,. An approach to the synthesis of gelsemine: the intramolecular reaction of an allylsilane with an acyliminium ion for the synthesis of one of the quaternary centers. Tetrahedron 1988; 44: 3931-3944.
28. Gouverneur VE, Houk KN, Pascal-Teresa B, Beno B, Janda KD, Lerner RA,. Control of the exo and endo pathways of the Diels-Alder reaction by antibody catalysis. Science 1993; 262: 204-208. (Pubitemid 23344463)
29. Chinchilla R, Falvello LR, Galindo N, Najera C,. Asymmetric synthesis of bicyclic α-amino acids by a Diels-Alder reaction to a new chriral α,β-dihydroalanine derivative. Tetrahedron: Asymmetry 1999; 10: 821-825. (Pubitemid 29191618)
30. Reynolds RC, Johnson CA, Piper J R, Sirotnak FM,. Synthesis and antifolate evaluation of the aminopterin analogue with a bicyclo[2.2.2]octane ring in place of the benzene ring. Eur J Med Chem 2001; 36: 237-242. (Pubitemid 32406199)
31. Kende AS, Lan J, Arad D,. regiospecific synthesis of a bridgehead-functionalized bicyclo[2.2.2]octenone. Tetrahedron Lett 2002; 43: 5237-5239. (Pubitemid 34717935)
32. Songis O Didierjean C, Martinez J, Calmès M,. Asymmetric Diels-Alder cycloaddition of 1-aminocyclohexadiene to chiral acrylate: synthesis of enantiopure bridgehead-aminobicyclo[2.2.2]octane-2-carboxylic acid derivatives. Eur J Org Chem 2007; 3166-3172.
33. Songis O, Géant P-Y, Sautrey G, Martinez J, Calmès M,. Asymmetric Diels-Alder reaction of aminodienes with a nonracemic acrylate bound to rink resin: a comparison of these reaction with their solution-state analogues. Eur J Org Chem 2008; 308-318.
34. Zand R, Sellinger OZ, Water R, Harris R,. α-aminocyclic and bicyclic alkane carboxylic acids: differential effects on selected amino acids of rat brain cortex. J Neurochem 1974; 23: 1201-1206.
35. Smith PW, Trivedi N, Howes PD, Sollis SL, Rahim G, Bethell RC, Lynn S,. Synthesis of a tetrasubstituted bicyclo [2.2.2] octane as a potential inhibitor of influenza virus sialidase. Bioorg Med Chem Lett 1999; 9: 611-614. (Pubitemid 29090663)
36. Chang L, Hagmann WK, MacCoss M,. PTC Int. Appl. WO 99/26615.
37. Synthesis of cyclic amino acid derivatives as cell adhesion inhibitors. Chem Abstr 1999; 131: 19301.
38. Chang L, Truong Q, Doss GA, MacCoss M, Lyon K, McCauley E, Mumford R, Forrest G, Vincent S, Schmidt JA, Hagmann WK,. Highly constrained bicyclic VLA-4 antagonists. Bioorg Med Chem Lett 2007; 17: 597-601. (Pubitemid 46108577)
39. Akkari R, Calmès M, Martinez J,. Toward Diels-Alder reactions on a solid support using polymer bound N-substituted 3-hydroxy-4,4-dimethyl-2- pyrrolidinone acrylate derivatives. Eur J Org Chem 2004; 2441-2450.
40. Akkari R, Calmès M, Escale F, Iapichella J, Rolland M, Martinez J,. (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid as a new chiral auxiliairy for solid phase asymmetric Diels-Alder reactions. Tetrahedron: Asymmetry 2004; 15: 2515-2525. (Pubitemid 39164146)
41. Calmès M, Didierjean C, Martinez J, Songis O,. (R)-4-(Benzyloxycarbonylphenyl)-3-hydroxy-4,4-dimethyl-2-pyrrolidinone) acrylate derivative as a chiral dienophile for the synthesis of enantiopure 2-aminocyclohexane carboxylic acids. Tetrahedron: Asymmetry 2005; 15: 2173-2178. (Pubitemid 40800227)
42. McGeary RP,. Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride. Tetrahedron Lett 1998; 39: 3319-3322. (Pubitemid 28198019)