메뉴 건너뛰기




Volumn 15, Issue 7, 2009, Pages 474-478

Regioselective and sequential reactivity of activated 2,5-diketopiperazines

Author keywords

Amino acid; Boc group; Diketopiperazines; Electrophilic reactivity; Lactam activation

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; PIPERAZINEDIONE;

EID: 67849128874     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1139     Document Type: Article
Times cited : (11)

References (37)
  • 1
    • 0037156593 scopus 로고    scopus 로고
    • Recent advances in the synthesis of diketopiperazines
    • Dinsmore CJ, Beshore DC. Recent advances in the synthesis of diketopiperazines. Tetrahedron 2002; 58: 3297-3312.
    • (2002) Tetrahedron , vol.58 , pp. 3297-3312
    • Dinsmore, C.J.1    Beshore, D.C.2
  • 2
    • 0037265516 scopus 로고    scopus 로고
    • Fischer PM. Diketopiperazines in peptide and combinatorial chemistry. J. Pept. Sci. 2003; 9: 9-35.
    • Fischer PM. Diketopiperazines in peptide and combinatorial chemistry. J. Pept. Sci. 2003; 9: 9-35.
  • 3
    • 0016593869 scopus 로고
    • Naturally occurring 2,5-dioxopiperazines and related compounds
    • Springler-Verlag: Vienna
    • Sammes PG. Naturally occurring 2,5-dioxopiperazines and related compounds. In Fortschritte der Chemie Organischer Naturstoffe. Springler-Verlag: Vienna, 1975; 51-118.
    • (1975) Fortschritte der Chemie Organischer Naturstoffe , pp. 51-118
    • Sammes, P.G.1
  • 4
    • 34547985546 scopus 로고    scopus 로고
    • Diketopiperazines: Biological activity and synthesis
    • Martins MB, Carvalho I. Diketopiperazines: biological activity and synthesis. Tetrahedron 2007; 63: 9923-9932.
    • (2007) Tetrahedron , vol.63 , pp. 9923-9932
    • Martins, M.B.1    Carvalho, I.2
  • 5
    • 1342306686 scopus 로고    scopus 로고
    • Du Y, Creighton CJ, Tounge BA, Reitz AB. Noncovalent self-assembly of bicyclo[4.2.2]diketopiperazines: influence of saturation in the bridging of carbacyclic ring. Org. Lett. 2004; 6: 309-312.
    • Du Y, Creighton CJ, Tounge BA, Reitz AB. Noncovalent self-assembly of bicyclo[4.2.2]diketopiperazines: influence of saturation in the bridging of carbacyclic ring. Org. Lett. 2004; 6: 309-312.
  • 6
    • 27444438386 scopus 로고    scopus 로고
    • Organic crystal engineering with 1,4-piperazine-2,5-diones. 6. Studies of the hydrogen-bond association of cyclo[(2-methylamino-4,7- dimethoxyindan-2-carboxylic acid)(2-amino-4,7-dimethoxyindan-2- carboxylic acid)]
    • Weatherhead-Kloster RA, Selby HD, MillerWB, Mash EA. Organic crystal engineering with 1,4-piperazine-2,5-diones. 6. Studies of the hydrogen-bond association of cyclo[(2-methylamino-4,7- dimethoxyindan-2-carboxylic acid)(2-amino-4,7-dimethoxyindan-2- carboxylic acid)]. J. Org. Chem. 2005; 70: 8693-8702.
    • (2005) J. Org. Chem , vol.70 , pp. 8693-8702
    • Weatherhead-Kloster, R.A.1    Selby, H.D.2    Miller, W.B.3    Mash, E.A.4
  • 7
    • 0000624398 scopus 로고
    • The cyclic dipeptide cyclo[(S)- phenylalanyl-(S)-histidyl] as a catalyst for asymmetric addition of hydrogen cyanide to aldehydes
    • Tanaka K, Mori A, Inoue S. The cyclic dipeptide cyclo[(S)- phenylalanyl-(S)-histidyl] as a catalyst for asymmetric addition of hydrogen cyanide to aldehydes. J. Org. Chem. 1990; 55: 181-185.
    • (1990) J. Org. Chem , vol.55 , pp. 181-185
    • Tanaka, K.1    Mori, A.2    Inoue, S.3
  • 8
    • 0029990764 scopus 로고    scopus 로고
    • Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide
    • Iyer MS, Gigstad KM, Namdev ND, Lipton M. Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide. J. Am. Chem. Soc. 1996; 118: 4910-4911.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 4910-4911
    • Iyer, M.S.1    Gigstad, K.M.2    Namdev, N.D.3    Lipton, M.4
  • 9
    • 0030914135 scopus 로고    scopus 로고
    • 2,5-Diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions
    • Le TXH, Bussolari JC, Murray WV. 2,5-Diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions. Tetrahedron Lett. 1997; 38: 3849-3852.
    • (1997) Tetrahedron Lett , vol.38 , pp. 3849-3852
    • TXH, L.1    Bussolari, J.C.2    Murray, W.V.3
  • 10
    • 84985516415 scopus 로고
    • Enantioselective synthesis of (R)-amino acids using L-valine as chiral agent
    • Schöllkopf U, Groth U, Deng C. Enantioselective synthesis of (R)-amino acids using L-valine as chiral agent. Angew. Chem. Int. Ed. Engl. 1981; 20: 798-799.
    • (1981) Angew. Chem. Int. Ed. Engl , vol.20 , pp. 798-799
    • Schöllkopf, U.1    Groth, U.2    Deng, C.3
  • 11
    • 0002776216 scopus 로고    scopus 로고
    • Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids
    • Bull SD, Davies SG, Epstein SW, Ouzman JVA. Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids. Chem. Commun. 1998; 659-660.
    • (1998) Chem. Commun , pp. 659-660
    • Bull, S.D.1    Davies, S.G.2    Epstein, S.W.3    Ouzman, J.V.A.4
  • 12
    • 33748718541 scopus 로고    scopus 로고
    • Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine
    • Bull SD, Davies SG, O'Shea MD. Stereoselective conjugate addition of organocuprates to a dehydroalanine derived diketopiperazine. J. Chem. Soc. Perkin Trans. I 1998; 3657-3658.
    • (1998) J. Chem. Soc. Perkin Trans. I , pp. 3657-3658
    • Bull, S.D.1    Davies, S.G.2    O'Shea, M.D.3
  • 13
    • 0032555634 scopus 로고    scopus 로고
    • Deracemisation of α-amino acids - and (S)-phenylalanine from the same enantiomer of a homochiral auxiliary
    • Bull SD, Davies SG, Epstein SW, Ouzman JVA. Deracemisation of α-amino acids - and (S)-phenylalanine from the same enantiomer of a homochiral auxiliary. Tetrahedron: Asymmetry 1998; 9: 2795-2798.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2795-2798
    • Bull, S.D.1    Davies, S.G.2    Epstein, S.W.3    Ouzman, J.V.A.4
  • 14
    • 0028054099 scopus 로고
    • Asymmetric syntheses of l-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines
    • Alcaraz C, Dolores Fernandez M, Pilar de Frutos M, Marco JL, Bernabe M, Foces-Foces C, Cano FH. Asymmetric syntheses of l-amino-2-phenyl(alkyl)cyclopropanecarboxylic acids by diastereoselective cyclopropanation of highly functionalized monochiral olefines. Tetrahedron 1994; 50: 12443-12456.
    • (1994) Tetrahedron , vol.50 , pp. 12443-12456
    • Alcaraz, C.1    Dolores Fernandez, M.2    Pilar de Frutos, M.3    Marco, J.L.4    Bernabe, M.5    Foces-Foces, C.6    Cano, F.H.7
  • 15
  • 17
    • 35048891074 scopus 로고    scopus 로고
    • Transannular rearrangement of activated lactams: Stereoselective synthesis of substituted pyrrolidine-2,4-diones from diketopiperazines
    • Farran D, Parrot I, Martinez J, Dewynter G. Transannular rearrangement of activated lactams: stereoselective synthesis of substituted pyrrolidine-2,4-diones from diketopiperazines. Angew. Chem. Int. Ed. Engl. 2007; 46: 7488-7490.
    • (2007) Angew. Chem. Int. Ed. Engl , vol.46 , pp. 7488-7490
    • Farran, D.1    Parrot, I.2    Martinez, J.3    Dewynter, G.4
  • 18
    • 36348999875 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of 2,4-diamino-3-hydroxyacids starting from diketopiperazines: A new route for the preparation of statine analogues
    • Farran D, Toupet L, Martinez J, Dewynter G. Stereocontrolled synthesis of 2,4-diamino-3-hydroxyacids starting from diketopiperazines: a new route for the preparation of statine analogues. Org. Lett. 2007; 9: 4833-4836.
    • (2007) Org. Lett , vol.9 , pp. 4833-4836
    • Farran, D.1    Toupet, L.2    Martinez, J.3    Dewynter, G.4
  • 19
    • 58149189066 scopus 로고    scopus 로고
    • Transannular rearrangement of activated 2,5-diketopiperazines: A key route to original scaffolds
    • Farran D, Parrot I, Toupet L, Martinez J, Dewynter G. Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds. Org. Biomol. Chem. 2008; 6: 3989-3996.
    • (2008) Org. Biomol. Chem , vol.6 , pp. 3989-3996
    • Farran, D.1    Parrot, I.2    Toupet, L.3    Martinez, J.4    Dewynter, G.5
  • 21
    • 0000794592 scopus 로고    scopus 로고
    • A facile preparation of enecarbamates
    • Dieter RK, Sharma RR. A facile preparation of enecarbamates. J. Org. Chem. 1996; 61: 4180-4184.
    • (1996) J. Org. Chem , vol.61 , pp. 4180-4184
    • Dieter, R.K.1    Sharma, R.R.2
  • 22
    • 0033592848 scopus 로고    scopus 로고
    • First asymmetric desymmetrisation of a centrosymmetric molecule: CBS reduction of a 2-pyridone [4 + 4]-photodimer derivative
    • Spivey AC, Andrews BI, Brown AD, Frampton CS. First asymmetric desymmetrisation of a centrosymmetric molecule: CBS reduction of a 2-pyridone [4 + 4]-photodimer derivative. Chem. Commun. 1999; 2523-2524.
    • (1999) Chem. Commun , pp. 2523-2524
    • Spivey, A.C.1    Andrews, B.I.2    Brown, A.D.3    Frampton, C.S.4
  • 23
    • 0037161860 scopus 로고    scopus 로고
    • The versatile conversion of acyclic amides to α-alkylated amines
    • Suh YG, Shin DY, Jung JK, Kim SH. The versatile conversion of acyclic amides to α-alkylated amines. Chem. Commun. 2002; 1064-1065.
    • (2002) Chem. Commun , pp. 1064-1065
    • Suh, Y.G.1    Shin, D.Y.2    Jung, J.K.3    Kim, S.H.4
  • 24
    • 84972822871 scopus 로고
    • Convenient preparation of dissymmetrical diesters of N-Boc glutamic acid
    • Schoenfelder A, Mann A. Convenient preparation of dissymmetrical diesters of N-Boc glutamic acid. Synthetic Comm. 1990; 20: 2585-2588.
    • (1990) Synthetic Comm , vol.20 , pp. 2585-2588
    • Schoenfelder, A.1    Mann, A.2
  • 25
    • 0025014988 scopus 로고
    • A new synthetic equivalent of the glutamic acid γ-anion and its application to the synthesis of S-(+)-γ-arboxyglutamic acid
    • Attwood MR, Carr MG, Jordan S. A new synthetic equivalent of the glutamic acid γ-anion and its application to the synthesis of S-(+)-γ-arboxyglutamic acid. Tetrahedron Lett. 1990; 31: 283-284.
    • (1990) Tetrahedron Lett , vol.31 , pp. 283-284
    • Attwood, M.R.1    Carr, M.G.2    Jordan, S.3
  • 26
    • 0027278425 scopus 로고
    • Regioselective ring opening of chiral N-Boc protected pyroglutamate and pyroaminoadipate ethyl esters with heteronucleophiles
    • Molina MT, Del Valle C, Escribano AM, Ezquerra J, Pedregal C. Regioselective ring opening of chiral N-Boc protected pyroglutamate and pyroaminoadipate ethyl esters with heteronucleophiles. Tetrahedron 1993; 49: 3801-3808.
    • (1993) Tetrahedron , vol.49 , pp. 3801-3808
    • Molina, M.T.1    Del Valle, C.2    Escribano, A.M.3    Ezquerra, J.4    Pedregal, C.5
  • 27
    • 0343932654 scopus 로고    scopus 로고
    • Solid phase synthesis of glutamic acid derivatives via nucleophilic ring opening of N-Boc pyroglutamate with heteronucleophiles
    • De Blas J, Dominguez E, Ezquerra J. Solid phase synthesis of glutamic acid derivatives via nucleophilic ring opening of N-Boc pyroglutamate with heteronucleophiles. Tetrahedron Lett. 2000; 41: 4567-4571.
    • (2000) Tetrahedron Lett , vol.41 , pp. 4567-4571
    • De Blas, J.1    Dominguez, E.2    Ezquerra, J.3
  • 28
    • 0037155516 scopus 로고    scopus 로고
    • Five- and six-membered ring opening of pyroglutamic diketopiperazine
    • Parrish DA, Mathias LJ. Five- and six-membered ring opening of pyroglutamic diketopiperazine. J. Org. Chem. 2002; 67: 1820-1826.
    • (2002) J. Org. Chem , vol.67 , pp. 1820-1826
    • Parrish, D.A.1    Mathias, L.J.2
  • 29
    • 85078063140 scopus 로고
    • α-tert-butoxycarbonyl α,ω-alkanediamine hydrochlorides from amino alcohols
    • α-tert-butoxycarbonyl α,ω-alkanediamine hydrochlorides from amino alcohols. Synthesis 1990; 366-368.
    • (1990) Synthesis , pp. 366-368
    • Mattingly, P.G.1
  • 30
    • 33644889303 scopus 로고
    • Selective reactions of azide-substituted α-diazo amides with olefins and alcohols using rhodium(II) catalysts
    • Jeganathan A, Richardson SK, Mani RS, Haley BE, Watt DS. Selective reactions of azide-substituted α-diazo amides with olefins and alcohols using rhodium(II) catalysts. J. Org. Chem. 1986; 51: 5362-5367.
    • (1986) J. Org. Chem , vol.51 , pp. 5362-5367
    • Jeganathan, A.1    Richardson, S.K.2    Mani, R.S.3    Haley, B.E.4    Watt, D.S.5
  • 31
    • 0033515621 scopus 로고    scopus 로고
    • An alkanesulfonamide "safety-catch'" linker for solid-phase synthesis
    • Backes BJ, Ellman JA. An alkanesulfonamide "safety-catch'" linker for solid-phase synthesis. J. Org. Chem. 1999; 64: 2322-2330.
    • (1999) J. Org. Chem , vol.64 , pp. 2322-2330
    • Backes, B.J.1    Ellman, J.A.2
  • 32
    • 0000117881 scopus 로고    scopus 로고
    • On the stabilization of the syn-rotamer of amino acid carbamate by hydrogen bonding
    • Marcovici-Mizrahi D, Gottlieb HE, Marks V, Nudelman A. On the stabilization of the syn-rotamer of amino acid carbamate by hydrogen bonding. J. Org. Chem. 1996; 61: 8402-8406.
    • (1996) J. Org. Chem , vol.61 , pp. 8402-8406
    • Marcovici-Mizrahi, D.1    Gottlieb, H.E.2    Marks, V.3    Nudelman, A.4
  • 35
    • 33748631301 scopus 로고    scopus 로고
    • Efficient, non-acidolytic method for the selective cleavage of N-Boc amino acid and peptide phenacyl esters linked to a polystyrene resin
    • Furlán RLE, Mata EG, Mascaretti OA. Efficient, non-acidolytic method for the selective cleavage of N-Boc amino acid and peptide phenacyl esters linked to a polystyrene resin. J. Chem. Soc. Perkin Trans. I 1998; 355-358.
    • (1998) J. Chem. Soc. Perkin Trans. I , pp. 355-358
    • Furlán, R.L.E.1    Mata, E.G.2    Mascaretti, O.A.3
  • 36
    • 39649110365 scopus 로고    scopus 로고
    • Sequence shuffle controls morphological consequences in a self-assembling tetrapeptide
    • Joshi KB, Verma S. Sequence shuffle controls morphological consequences in a self-assembling tetrapeptide. J. Pept. Sci. 2008; 14: 118-126.
    • (2008) J. Pept. Sci , vol.14 , pp. 118-126
    • Joshi, K.B.1    Verma, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.