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Volumn 41, Issue 14, 2011, Pages 2036-2043

A flexible approach to protected (4S,5S)-5-alkyl-1-benzyl-4-benzyloxy-2- pyrrolidinones

Author keywords

2 pyrrolidinone; Diastereoselective reduction; Zn(BH4)2

Indexed keywords

1 BENZYL 4 BENZYLOXY 5 (I BUTYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 (N BUTYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 (N HEPTADECANYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 (N HEXADECYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 (N OCTYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 (N PENTYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 (N PROPYL) 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 ETHYL 2 PYRROLIDINONE; 1 BENZYL 4 BENZYLOXY 5 METHYL 2 PYRROLIDINONE; 2 PYRROLIDONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79957631933     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.495827     Document Type: Article
Times cited : (2)

References (32)
  • 1
    • 0004175604 scopus 로고
    • For reviews on the occurrence, biological properties, and syntheses of pyrrolidines, see (a), A. Brossi, (Ed.); Academic Press: New York, Chapter 6
    • For reviews on the occurrence, biological properties, and syntheses of pyrrolidines, see (a) Numata, A.; Ibuka, T. In The Alkaloids; A. Brossi, (Ed.); Academic Press: New York, 1987; vol. 31, Chapter 6;
    • (1987) The Alkaloids , vol.31
    • Numata, A.1    Ibuka, T.2
  • 3
    • 0031463959 scopus 로고    scopus 로고
    • Pyrrole, pyrrolidine, pyridine, piperidine, azepine and tropane alkaloids
    • O'Hagan, D. Pyrrole, pyrrolidine, pyridine, piperidine, azepine and tropane alkaloids. Nat. Prod. Rep. 1997, 14, 637-651; (Pubitemid 28010216)
    • (1997) Natural Product Reports , vol.14 , Issue.6 , pp. 637-651
    • O'Hagan, D.1
  • 4
    • 0032856633 scopus 로고    scopus 로고
    • Pyrrolizidine alkaloids
    • Liddell, J. M. Pyrrolizidine alkaloids. Nat. Prod. Rep. 1999, 16, 499-507;
    • (1999) Nat. Prod. Rep. , vol.16 , pp. 499-507
    • Liddell, J.M.1
  • 5
    • 0035925104 scopus 로고    scopus 로고
    • Polyhydroxylated alkaloids - Natural occurrence and therapeutic applications
    • DOI 10.1016/S0031-9422(00)00451-9, PII S0031942200004519
    • Watson, A. A.; Fleet, G. W. J.; Asano, N.; Molyneux, R. J.; Nash, R. J. Polyhydroxylated alkaloids-natural occurrence and therapeutic applications. Phytochemistry 2001, 56, 265-295; (Pubitemid 32162799)
    • (2001) Phytochemistry , vol.56 , Issue.3 , pp. 265-295
    • Watson, A.A.1    Fleet, G.W.J.2    Asano, N.3    Molyneux, R.J.4    Nash, R.J.5
  • 6
    • 0034607947 scopus 로고    scopus 로고
    • Sugar-mimic glycosidase inhibitors: Natural occurrence, biological activity and prospects for therapeutic application
    • DOI 10.1016/S0957-4166(00)00113-0, PII S0957416600001130
    • Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Sugar-mimic glycosidase inhibitors: Natural occurrence, biological activity, and prospects for therapeutic application. Tetrahedron: Asymmetry 2000, 11, 1645-1680. (Pubitemid 30320886)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.8 , pp. 1645-1680
    • Asano, N.1    Nash, R.J.2    Molyneux, R.J.3    Fleet, G.W.J.4
  • 7
    • 0028545703 scopus 로고
    • Five-membered ring azasugars as potent inhibitors of a-L-rhamnosidase (naringinase) from Penicillium decumbens
    • Provencher, L.; Steensma, D. H.; Wong, C. H. Five-membered ring azasugars as potent inhibitors of a-L-rhamnosidase (naringinase) from Penicillium decumbens. Bioorg. Med. Chem. 1994, 2, 1179-1188;
    • (1994) Bioorg. Med. Chem. , vol.2 , pp. 1179-1188
    • Provencher, L.1    Steensma, D.H.2    Wong, C.H.3
  • 8
    • 0033800019 scopus 로고    scopus 로고
    • Synthesis of potent α-D-mannosidase and α-L-fucosidase inhibitors: 4-Amino-4-deoxy- D-erythrose and 4-amino-4,5-dideoxy-L-lyxose
    • Joubert, M.; Defoin, A.; Tarnus, C.; Streith, J. Synthesis of potent α-D-mannosidase and α-L-fucosidase inhibitors: 4-Amino-4-deoxy- D-erythrose and 4-amino-4,5-dideoxy-L-lyxose. Synlett 2000, 1366-1368.
    • (2000) Synlett , pp. 1366-1368
    • Joubert, M.1    Defoin, A.2    Tarnus, C.3    Streith, J.4
  • 9
    • 0000538619 scopus 로고
    • Anisomycin a new anti-protozoan antibiotic
    • Sobin, B. A.; Tanner Jr., F. W. Anisomycin, a new anti-protozoan antibiotic. J. Am. Chem. Soc. 1954, 76, 4053.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 4053
    • Sobin, B.A.1    Tanner, Jr.F.W.2
  • 10
    • 0002846339 scopus 로고
    • Anisomycin and related antibiotics
    • F. E. Hahn (Ed.), Springer Verlag; Berlin
    • Jimenez, A.; Vazquez, D. Anisomycin and related antibiotics. In Antibiotics; F. E. Hahn (Ed.), Springer Verlag; Berlin, 1979; pp. 1-19.
    • (1979) Antibiotics , pp. 1-19
    • Jimenez, A.1    Vazquez, D.2
  • 11
    • 33846963550 scopus 로고    scopus 로고
    • Marked small molecule libraries: A truncated approach to molecular probe design
    • For recent examples, see (b)
    • For recent examples, see (b) Inverarity, I. A.; Hulme, A. N. Marked small molecule libraries: A truncated approach to molecular probe design. Org. Biomol. Chem. 2007, 5, 636-643.
    • (2007) Org. Biomol. Chem. , Issue.5 , pp. 636-643
    • Inverarity, I.A.1    Hulme, A.N.2
  • 12
    • 0031053190 scopus 로고    scopus 로고
    • Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 12. Synthesis of (-)-platynecine
    • DOI 10.1021/jo961919x, PII S0022326396019196
    • Denmark, S. E.; Parker Jr., D. L.; Dixon, J. A. Tandem [4+2]/[3+2] cycloadditions of nitroalkenes, 12: Synthesis of (-)-platynecine. J. Org. Chem. 1997, 62, 435-436; (Pubitemid 27089019)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.2 , pp. 435-436
    • Denmark, S.E.1    Parker Jr., D.L.2    Dixon, J.A.3
  • 13
    • 0031013935 scopus 로고    scopus 로고
    • An enantiocontrolled synthesis of pyrrolizidines, (-)-platynecine and (-)-hadinecine
    • DOI 10.1016/S0040-4039(96)02371-4, PII S0040403996023714
    • Kang, S. H.; Kim, G. T.; Yoo, Y. S. An enantiocontrolled synthesis of pyrrolizidines, (-)-platynecine and (-)-hadinecine. Tetrahedron Lett. 1997, 38, 603-606; (Pubitemid 27046648)
    • (1997) Tetrahedron Letters , vol.38 , Issue.4 , pp. 603-606
    • Kang, S.H.1    Kim, G.T.2    Yoo, Y.S.3
  • 14
    • 37049072184 scopus 로고
    • A stereocontrolled route to both enantiomers of the necine base dihydroxyheliotridane via intramolecular 1,3-dipolar addition using the same chiral precursor
    • Hashimura, K.; Tomita, S.; Hiroya, K.; Ogasawara, K. A stereocontrolled route to both enantiomers of the necine base dihydroxyheliotridane via intramolecular 1,3-dipolar addition using the same chiral precursor. J. Chem. Soc. Chem. Commun. 1995, 2291-2292.
    • (1995) J. Chem. Soc. Chem. Commun. , pp. 2291-2292
    • Hashimura, K.1    Tomita, S.2    Hiroya, K.3    Ogasawara, K.4
  • 15
    • 0037134295 scopus 로고    scopus 로고
    • Regio- and stereoselective ring opening of epoxides. Enantioselective synthesis of 2,3,4-trisubstituted five-membered heterocycles
    • DOI 10.1016/S0957-4166(02)00160-X, PII S095741660200160X
    • For selected examples, see (a) Diez, D.; Beneitez, M. T.; Marcos, I. S.; Garrido, N. M.; Basabe, P.; Urones, J. G. Regio- and stereoselective ring opening of epoxides: Enantioselective synthesis of 2,3,4-trisubstituted five-membered heterocycles. Tetrahedron: Asymmetry 2002, 13, 639-646; (Pubitemid 34465528)
    • (2002) Tetrahedron Asymmetry , vol.13 , Issue.6 , pp. 639-646
    • Diez, D.1    Beneitez M.Templo2    Marcos, I.S.3    Garrido, N.M.4    Basabe, P.5    Urones, J.G.6
  • 16
    • 2942669882 scopus 로고    scopus 로고
    • Nitrone in L-lyxose series: Cycloaddition way for the synthesis of new C-α-fucosides
    • DOI 10.1016/j.tetlet.2004.05.075, PII S004040390401127X
    • Chevrier, C.; LeNouen, D.; Neuburger, M.; Defoina, A.; Tarnusa, C. Nitrone in L-lyxose series: Cycloaddition way for the synthesis of new C-α-fucosides. Tetrahedron Lett. 2004, 45, 5363-5366. (Pubitemid 38781855)
    • (2004) Tetrahedron Letters , vol.45 , Issue.28 , pp. 5363-5366
    • Chevrier, C.1    LeNouen, D.2    Neuburger, M.3    Defoin, A.4    Tarnus, C.5
  • 17
    • 0032497681 scopus 로고    scopus 로고
    • An easy access to protected (4S, 5R)-5-alkyl-4-hydroxy-2-pyrrolidinones and their use as versatile synthetic intermediates
    • PII S0040402098007340
    • Huang, P. Q.; Wang, S. L.; Ye, J. L.; Ruan, Y. P.; Huang, Y. Q.; Zheng, H.; Gao, J. X. An easy access to protected (4S,5R)-5-alkyl-4-hydroxy-2- pyrrolidinones and their use as versatile synthetic intermediates. Tetrahedron 1998, 54, 12547-12560. (Pubitemid 28552694)
    • (1998) Tetrahedron , vol.54 , Issue.41 , pp. 12547-12560
    • Huang, P.Q.1    Wang, S.L.2    Ye, J.L.3    Ruan, Y.P.4    Huang, Y.Q.5    Zheng, H.6    Gao, J.X.7
  • 18
    • 33744462355 scopus 로고    scopus 로고
    • Asymmetric synthesis of hydroxylated pyrrolidines, piperidines, and related bioactive compounds: From N-acyliminium chemistry to N-α-carbanion chemistry
    • For two accounts, see (a)
    • For two accounts, see (a) Huang, P. Q. Asymmetric synthesis of hydroxylated pyrrolidines, piperidines, and related bioactive compounds: From N-acyliminium chemistry to N-α-carbanion chemistry. Synlett 2006, 1133-1149;
    • (2006) Synlett , pp. 1133-1149
    • Huang, P.Q.1
  • 19
    • 33846064594 scopus 로고    scopus 로고
    • Recent advances on the asymmetric synthesis of bioactive 2-pyrrolidinone-related compounds starting from enantiomeric malic acid, in new methods for the asymmetric synthesis of nitrogen heterocycles
    • J. L. Vicario, D. Badia, and L. Carillo (Eds.); Research Signpost: Kerala
    • Huang, P. Q. Recent advances on the asymmetric synthesis of bioactive 2-pyrrolidinone-related compounds starting from enantiomeric malic acid, in new methods for the asymmetric synthesis of nitrogen heterocycles. In New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles; J. L. Vicario, D. Badia, and L. Carillo (Eds.); Research Signpost: Kerala, 2005; pp. 197-222.
    • (2005) New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles , pp. 197-222
    • Huang, P.Q.1
  • 20
    • 70349194488 scopus 로고    scopus 로고
    • A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: Asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine
    • Xiang, S.-H.; Yuan, H.-Q.; Huang, P.-Q. A versatile approach to cis-5-substituted 4-hydroxy-2-pyrrolidinones: Asymmetric synthesis of angiogenesis inhibitor streptopyrrolidine. Tetrahedron: Asymmetry 2009, 20, 2020-2026.
    • (2009) Tetrahedron: Asymmetry , vol.20 , pp. 2020-2026
    • Xiang, S.-H.1    Yuan, H.-Q.2    Huang, P.-Q.3
  • 21
    • 33744863869 scopus 로고
    • An introduction of chiral centers into acyclic systems based on stereoselective ketone reduction
    • 2, see (a)
    • 2, see (a) Oishi, T.; Nakata, T. An introduction of chiral centers into acyclic systems based on stereoselective ketone reduction. Acc. Chem. Res. 1984, 17, 338-344;
    • (1984) Acc. Chem. Res. , vol.17 , pp. 338-344
    • Oishi, T.1    Nakata, T.2
  • 22
    • 0041891552 scopus 로고
    • Zinc borohydride a reducing agent with high potential
    • Ranu, B. C. Zinc borohydride, a reducing agent with high potential. Synlett 1993, 885-892;
    • (1993) Synlett , pp. 885-892
    • Ranu, B.C.1
  • 23
    • 0032437327 scopus 로고    scopus 로고
    • Synthetic applications of zinc borohydride
    • Narasimhan, S.; Balakumar, R. Synthetic applications of zinc borohydride. Aldrichim. Acta 1998, 31, 19-26. (Pubitemid 128335503)
    • (1998) Aldrichimica Acta , vol.31 , Issue.1 , pp. 19-26
    • Narasimhan, S.1    Balakumar, R.2
  • 24
    • 0032542161 scopus 로고    scopus 로고
    • Simple transformation of nitrile into ester by the use of chlorotrimethylsilane
    • PII S0040403998021431
    • Luo, F.-T.; Jeevanandam, A. Simple transformation of nitrile into ester by the use of chlorotrimethylsilane. Tetrahedron Lett. 1998, 39, 9455-9456; (Pubitemid 28541104)
    • (1998) Tetrahedron Letters , vol.39 , Issue.51 , pp. 9455-9456
    • Luo, F.-T.1    Jeevanandam, A.2
  • 25
    • 0026785343 scopus 로고
    • A novel and unusual reaction of enol ethers with banzyltriethylammonium borohydride and chlorotrimethylsilane
    • Baskaran, S.; Chidambaram, N.; Narasimhan, N.; Chandrasekaran, S. A novel and unusual reaction of enol ethers with banzyltriethylammonium borohydride and chlorotrimethylsilane. Tetrahedron Lett. 1992, 33, 6371-6374;
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6371-6374
    • Baskaran, S.1    Chidambaram, N.2    Narasimhan, N.3    Chandrasekaran, S.4
  • 26
    • 0026741964 scopus 로고
    • Observations on the selective deoxygenation of epoxides to olefins with chlorotrimethylsilane and zinc
    • Afonso, C. A. M.; Motherwell, W. B.; Roberts, L. R. Observations on the selective deoxygenation of epoxides to olefins with chlorotrimethylsilane and zinc. Tetrahedron Lett. 1992, 33, 3367-3370;
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3367-3370
    • Afonso, C.A.M.1    Motherwell, W.B.2    Roberts, L.R.3
  • 27
    • 0009681830 scopus 로고
    • Rapid high-yield cleavage of enol and dienol methyl ethers under mild conditions using chlorotrimethylsilane/sodium iodide
    • Kosarych, Z.; Cohen, T. Rapid, high-yield cleavage of enol and dienol methyl ethers under mild conditions using chlorotrimethylsilane/sodium iodide. Tetrahedron Lett. 1980, 21, 3959-3962.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3959-3962
    • Kosarych, Z.1    Cohen, T.2
  • 28
    • 57749093091 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones to their corresponding amines with N-methylpyrrolidine zinc borohydride
    • Alinezhad, H.; Tajbakhsh, M.; Salehian, F.; Fazli, K. Reductive amination of aldehydes and ketones to their corresponding amines with N-methylpyrrolidine zinc borohydride. Tetrahedron Lett. 2009, 50, 659-661;
    • (2009) Tetrahedron Lett. , vol.50 , pp. 659-661
    • Alinezhad, H.1    Tajbakhsh, M.2    Salehian, F.3    Fazli, K.4
  • 30
    • 63549084926 scopus 로고    scopus 로고
    • Chemo- and diastereoselective control for a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones
    • Liu, L.-X.; Xiao, K.-J.; Huang, P.-Q. Chemo- and diastereoselective control for a flexible approach to (5S,6S)-6-alkyl-5-benzyloxy-2-piperidinones. Tetrahedron 2009, 65, 3834-3841.
    • (2009) Tetrahedron , vol.65 , pp. 3834-3841
    • Liu, L.-X.1    Xiao, K.-J.2    Huang, P.-Q.3
  • 31
    • 0025121014 scopus 로고
    • Stereoselective synthesis of statin analogues
    • DOI 10.1016/S0040-4039(00)97777-3
    • Bernardi, A.; Micheli, F.; Potenza, D.; Scolastico, C.; Villa, R. Stereoselective synthesis of statin analogues. Tetrahedron Lett. 1990, 31, 4949-4952. (Pubitemid 20251253)
    • (1990) Tetrahedron Letters , vol.31 , Issue.34 , pp. 4949-4952
    • Bernardi, A.1    Micheli, F.2    Potenza, D.3    Scolastico, C.4    Villa, R.5
  • 32
    • 33846107960 scopus 로고    scopus 로고
    • Mechanism for the regioselective asymmetric addition of Grignard reagents to malimides: A computational exploration
    • DOI 10.1021/jo0613683
    • Ye, J.-L., Huang, P.-Q., Lu, X. Mechanism for the regioselective asymmetric addition of Grignard reagents to malimides: A computational exploration. J. Org. Chem. 2007, 72, 35-42. (Pubitemid 46068201)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.1 , pp. 35-42
    • Ye, J.-L.1    Huang, P.-Q.2    Lu, X.3


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