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Volumn 108, Issue 17, 2011, Pages 6745-6750

Solid-phase synthesis and chemical space analysis of a 190-membered alkaloid/terpenoid-like library

Author keywords

Asymmetric synthesis; Cheminformatics; Diversity oriented synthesis; Multiscaffold library

Indexed keywords

ALKALOID; ALKYNE DERIVATIVE; AMINE; BUTANE; ENEDIYNE; METAL; NATURAL PRODUCT; SILANE DERIVATIVE; SULFINAMIDE; SULFONAMIDE; TERPENOID;

EID: 79955563074     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1015268108     Document Type: Article
Times cited : (36)

References (45)
  • 1
    • 33644839988 scopus 로고    scopus 로고
    • Diversity-oriented synthesis: Exploring the intersections between chemistry and biology
    • Tan DS (2005) Diversity-oriented synthesis: Exploring the intersections between chemistry and biology. Nat Chem Biol 1:74-84.
    • (2005) Nat Chem Biol , vol.1 , pp. 74-84
    • Tan, D.S.1
  • 3
    • 77952545822 scopus 로고    scopus 로고
    • Expanding the range of "druggable" targets with natural product-based libraries: An academic perspective
    • Bauer RA, Wurst JM, Tan DS (2010) Expanding the range of "druggable" targets with natural product-based libraries: An academic perspective. Curr Opin Chem Biol 14:308-314.
    • (2010) Curr Opin Chem Biol , vol.14 , pp. 308-314
    • Bauer, R.A.1    Wurst, J.M.2    Tan, D.S.3
  • 4
    • 44949134801 scopus 로고    scopus 로고
    • The impact of natural products upon modern drug discovery
    • Ganesan A (2008) The impact of natural products upon modern drug discovery. Curr Opin Chem Biol 12:306-317.
    • (2008) Curr Opin Chem Biol , vol.12 , pp. 306-317
    • Ganesan, A.1
  • 5
    • 0042844744 scopus 로고    scopus 로고
    • Natural products as sources of new drugs over the period 1981-2002
    • Newman DJ, Cragg GM, Snader KM (2003) Natural products as sources of new drugs over the period 1981-2002. J Nat Prod 66:1022-1037.
    • (2003) J Nat Prod , vol.66 , pp. 1022-1037
    • Newman, D.J.1    Cragg, G.M.2    Snader, K.M.3
  • 6
    • 77952477596 scopus 로고    scopus 로고
    • Privileged scaffolds for library design and drug discovery
    • Welsch ME, Snyder SA, Stockwell BR (2010) Privileged scaffolds for library design and drug discovery. Curr Opin Chem Biol 14:347-361.
    • (2010) Curr Opin Chem Biol , vol.14 , pp. 347-361
    • Welsch, M.E.1    Snyder, S.A.2    Stockwell, B.R.3
  • 7
    • 2942590399 scopus 로고    scopus 로고
    • Libraries from natural product-like scaffolds
    • Boldi AM (2004) Libraries from natural product-like scaffolds. Curr Opin Chem Biol 8:281-286.
    • (2004) Curr Opin Chem Biol , vol.8 , pp. 281-286
    • Boldi, A.M.1
  • 8
    • 4544326369 scopus 로고    scopus 로고
    • Synthetic strategy toward skeletal diversity via solid-supported, otherwise unstable reactive intermediates
    • Taylor SJ, Taylor AM, Schreiber SL (2004) Synthetic strategy toward skeletal diversity via solid-supported, otherwise unstable reactive intermediates. Angew Chem Int Ed 43:1681-1685.
    • (2004) Angew Chem Int Ed , vol.43 , pp. 1681-1685
    • Taylor, S.J.1    Taylor, A.M.2    Schreiber, S.L.3
  • 9
    • 10344242467 scopus 로고    scopus 로고
    • A library of spirooxindoles based on a stereoselective three-component coupling reaction
    • Lo MMC, Neumann CS, Nagayama S, Perlstein EO, Schreiber SL (2004) A library of spirooxindoles based on a stereoselective three-component coupling reaction. J Am Chem Soc 126:16077-16086.
    • (2004) J Am Chem Soc , vol.126 , pp. 16077-16086
    • Lo, M.M.C.1    Neumann, C.S.2    Nagayama, S.3    Perlstein, E.O.4    Schreiber, S.L.5
  • 10
    • 12344293904 scopus 로고    scopus 로고
    • Skeletal diversity via a folding pathway: Synthesis of indole alkaloid-like skeletons
    • Oguri H, Schreiber SL (2005) Skeletal diversity via a folding pathway: Synthesis of indole alkaloid-like skeletons. Org Lett 7:47-50.
    • (2005) Org Lett , vol.7 , pp. 47-50
    • Oguri, H.1    Schreiber, S.L.2
  • 12
    • 77951837637 scopus 로고    scopus 로고
    • The tert-butylsulfinamide lynchpin in transition metal-mediated multiscaffold library synthesis
    • Bauer RA, DiBlasi CM, Tan DS (2010) The tert-butylsulfinamide lynchpin in transition metal-mediated multiscaffold library synthesis. Org Lett 12:2084-2087.
    • (2010) Org Lett , vol.12 , pp. 2084-2087
    • Bauer, R.A.1    DiBlasi, C.M.2    Tan, D.S.3
  • 13
    • 2942565810 scopus 로고    scopus 로고
    • Natural products and combinatorial chemistry: Back to the future
    • Ortholand JY, Ganesan A (2004) Natural products and combinatorial chemistry: Back to the future. Curr Opin Chem Biol 8:271-280.
    • (2004) Curr Opin Chem Biol , vol.8 , pp. 271-280
    • Ortholand, J.Y.1    Ganesan, A.2
  • 14
    • 63049135096 scopus 로고    scopus 로고
    • tert-Butanesulfinimines: Structure, synthesis, and synthetic applications
    • Ferreira F, Botuha C, Chemla F, Pérez-Luna A (2009) tert-Butanesulfinimines: Structure, synthesis, and synthetic applications. Chem Soc Rev 38:1162-1186.
    • (2009) Chem Soc Rev , vol.38 , pp. 1162-1186
    • Ferreira, F.1    Botuha, C.2    Chemla, F.3    Pérez-Luna, A.4
  • 15
    • 18844401383 scopus 로고    scopus 로고
    • An acid-stable tert-butyldiarylsilyl (TBDAS) linker for solid-phase organic synthesis
    • DiBlasi CM, Macks DE, Tan DS (2005) An acid-stable tert-butyldiarylsilyl (TBDAS) linker for solid-phase organic synthesis. Org Lett 7:1777-1780.
    • (2005) Org Lett , vol.7 , pp. 1777-1780
    • DiBlasi, C.M.1    Macks, D.E.2    Tan, D.S.3
  • 16
    • 33744491803 scopus 로고    scopus 로고
    • Highly diastereoselective synthesis of N- tert- butylsulfinylpropargylamines through direct addition of alkynes to N-tertbutanesulfinimines
    • Ding CH, Chen DD, Luo ZB, Dai LX, Hou XL (2006) Highly diastereoselective synthesis of N- tert-butylsulfinylpropargylamines through direct addition of alkynes to N-tertbutanesulfinimines. Synlett 1272-1274.
    • (2006) Synlett , pp. 1272-1274
    • Ding, C.H.1    Chen, D.D.2    Luo, Z.B.3    Dai, L.X.4    Hou, X.L.5
  • 17
    • 75749144634 scopus 로고    scopus 로고
    • Highly diastereoselective addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl aldimines: A practical and general access to chiral α-branched amines
    • Chen BL, Wang B, Lin GQ (2010) Highly diastereoselective addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl aldimines: A practical and general access to chiral α-branched amines. J Org Chem 75:941-944.
    • (2010) J Org Chem , vol.75 , pp. 941-944
    • Chen, B.L.1    Wang, B.2    Lin, G.Q.3
  • 18
    • 33644784912 scopus 로고    scopus 로고
    • Asymmetric addition reactions of Grignard reagents to chiral 2-trifluoromethyl tert-butyl (Ellman) sulfinimineethanol adducts
    • Kuduk SD, Marco CND, Pitzenberger SM, Tsou N (2006) Asymmetric addition reactions of Grignard reagents to chiral 2-trifluoromethyl tert-butyl (Ellman) sulfinimineethanol adducts. Tetrahedron Lett 47:2377-2381.
    • (2006) Tetrahedron Lett , vol.47 , pp. 2377-2381
    • Kuduk, S.D.1    Marco, C.N.D.2    Pitzenberger, S.M.3    Tsou, N.4
  • 19
    • 0035101886 scopus 로고    scopus 로고
    • Asymmetric Pauson-Khand reactions of chiral sulfinamides: Asymmetric synthesis of 3-azabicyclo[3.3.0]oct-5-en-7-one derivatives
    • Hiroi K, Watanabe T (2001) Asymmetric Pauson-Khand reactions of chiral sulfinamides: Asymmetric synthesis of 3-azabicyclo[3.3.0]oct-5-en-7-one derivatives. Heterocycles 54:73-76.
    • (2001) Heterocycles , vol.54 , pp. 73-76
    • Hiroi, K.1    Watanabe, T.2
  • 20
    • 67049134276 scopus 로고    scopus 로고
    • Advances in solution- and solid-phase synthesis toward the generation of natural product-like libraries
    • Nandy JP, et al. (2009) Advances in solution- and solid-phase synthesis toward the generation of natural product-like libraries. Chem Rev 109:1999-2060.
    • (2009) Chem Rev , vol.109 , pp. 1999-2060
    • Nandy, J.P.1
  • 21
    • 18244392211 scopus 로고    scopus 로고
    • Enantioselective reductive cyclization of 1,6-enynes via rhodium-catalyzed asymmetric hydrogenation: C-C bond formation precedes hydrogen activation
    • Jang HY, et al. (2005) Enantioselective reductive cyclization of 1,6-enynes via rhodium-catalyzed asymmetric hydrogenation: C-C bond formation precedes hydrogen activation. J Am Chem Soc 127:6174-6175.
    • (2005) J Am Chem Soc , vol.127 , pp. 6174-6175
    • Jang, H.Y.1
  • 22
    • 0037205927 scopus 로고    scopus 로고
    • Intermolecular transition metalcatalyzed [4 + 2 + 2] cycloaddition reactions: A new approach to the construction of eight-membered rings
    • Evans PA, Robinson JE, Baum EW, Fazal AN (2002) Intermolecular transition metalcatalyzed [4 + 2 + 2] cycloaddition reactions: A new approach to the construction of eight-membered rings. J Am Chem Soc 124:8782-8783.
    • (2002) J Am Chem Soc , vol.124 , pp. 8782-8783
    • Evans, P.A.1    Robinson, J.E.2    Baum, E.W.3    Fazal, A.N.4
  • 23
    • 1842483218 scopus 로고    scopus 로고
    • Enyne metathesis (enyne bond reorganization)
    • Diver ST, Giessert AJ (2004) Enyne metathesis (enyne bond reorganization). Chem Rev 104:1317-1382.
    • (2004) Chem Rev , vol.104 , pp. 1317-1382
    • Diver, S.T.1    Giessert, A.J.2
  • 24
    • 0038545118 scopus 로고    scopus 로고
    • Sequences of yne-ene cross metathesis and Diels-Alder cycloaddition reactions - Modular solid-phase synthesis of substituted octahydrobenzazepinones
    • Schurer SC, Blechert S (1999) Sequences of yne-ene cross metathesis and Diels-Alder cycloaddition reactions - Modular solid-phase synthesis of substituted octahydrobenzazepinones. Synlett 1879-1882.
    • (1999) Synlett , pp. 1879-1882
    • Schurer, S.C.1    Blechert, S.2
  • 25
    • 0038206363 scopus 로고    scopus 로고
    • Synthesis of pseudo-oligosaccharides by a sequence of yne-ene cross metathesis and Diels-Alder reaction
    • Schurer SC, Blechert S (1999) Synthesis of pseudo-oligosaccharides by a sequence of yne-ene cross metathesis and Diels-Alder reaction. Chem Commun 1203-1204.
    • (1999) Chem Commun , pp. 1203-1204
    • Schurer, S.C.1    Blechert, S.2
  • 26
    • 12944303660 scopus 로고    scopus 로고
    • Cp*RuCl-catalyzed [2 + 2 + 2] cycloadditions of α,ω-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles
    • Yamamoto Y, et al. (2005) Cp*RuCl-catalyzed [2 + 2 + 2] cycloadditions of α,ω-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles. J Am Chem Soc 127:605-613.
    • (2005) J Am Chem Soc , vol.127 , pp. 605-613
    • Yamamoto, Y.1
  • 27
    • 34447298389 scopus 로고    scopus 로고
    • A general approach to chemo- and regioselective cyclotrimerization reactions
    • Young DD, Deiters A (2007) A general approach to chemo- and regioselective cyclotrimerization reactions. Angew Chem Int Ed 46:5187-5190.
    • (2007) Angew Chem Int Ed , vol.46 , pp. 5187-5190
    • Young, D.D.1    Deiters, A.2
  • 28
    • 33748550638 scopus 로고    scopus 로고
    • Cationic rhodium(I)/modified-BINAP catalyzed [2 + 2 + 2] cycloaddition of alkynes with nitriles
    • Tanaka K, Suzuki N, Nishida G (2006) Cationic rhodium(I)/modified-BINAP catalyzed [2 + 2 + 2] cycloaddition of alkynes with nitriles. Eur J Org Chem 3917-3922.
    • (2006) Eur J Org Chem , pp. 3917-3922
    • Tanaka, K.1    Suzuki, N.2    Nishida, G.3
  • 29
    • 66449091225 scopus 로고    scopus 로고
    • 8-BINAP complex catalyzed [2 + 2 + 2] cycloadditions of 1,6- and 1,7-diynes with carbonyl compounds
    • 8-BINAP complex catalyzed [2 + 2 + 2] cycloadditions of 1,6- and 1,7-diynes with carbonyl compounds. Eur J Org Chem 2737-2747.
    • (2009) Eur J Org Chem , pp. 2737-2747
    • Otake, Y.1    Tanaka, R.2    Tanaka, K.3
  • 30
    • 33644886020 scopus 로고    scopus 로고
    • Pyridines via solid-supported [2 + 2 + 2] cyclotrimerization
    • Senaiar RS, Young DD, Deiters A (2006) Pyridines via solid-supported [2 + 2 + 2] cyclotrimerization. Chem Commun 1313-1315.
    • (2006) Chem Commun , pp. 1313-1315
    • Senaiar, R.S.1    Young, D.D.2    Deiters, A.3
  • 31
    • 34047128046 scopus 로고    scopus 로고
    • Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and diynes. Synthesis of 7,6- and 7,5-fused bicyclic compounds
    • Maeda K, Saito S (2007) Nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and diynes. Synthesis of 7,6- and 7,5-fused bicyclic compounds. Tetrahedron Lett 48:3173-3176.
    • (2007) Tetrahedron Lett , vol.48 , pp. 3173-3176
    • Maeda, K.1    Saito, S.2
  • 32
    • 0029084414 scopus 로고
    • A new general method for preparation of N-methoxy- N-methylamides. Application in direct conversion of an ester to a ketone
    • Williams JM, et al. (1995) A new general method for preparation of N-methoxy- N-methylamides. Application in direct conversion of an ester to a ketone. Tetrahedron Lett 36:5461-5464.
    • (1995) Tetrahedron Lett , vol.36 , pp. 5461-5464
    • Williams, J.M.1
  • 33
    • 0002307453 scopus 로고
    • The Pauson-Khand cycloaddition reaction for synthesis of cyclopentenones
    • Schore NE (1991) The Pauson-Khand cycloaddition reaction for synthesis of cyclopentenones. Org React 40:1-90.
    • (1991) Org React , vol.40 , pp. 1-90
    • Schore, N.E.1
  • 34
    • 0036008853 scopus 로고    scopus 로고
    • Pathway development and pilot library realization in diversity-oriented synthesis. Exploring Ferrier and Pauson- Khand reactions on a glycal template
    • Kubota H, Lim J, Depew KM, Schreiber SL (2002) Pathway development and pilot library realization in diversity-oriented synthesis. Exploring Ferrier and Pauson- Khand reactions on a glycal template. Chem Biol 9:265-276.
    • (2002) Chem Biol , vol.9 , pp. 265-276
    • Kubota, H.1    Lim, J.2    Depew, K.M.3    Schreiber, S.L.4
  • 35
    • 0142025317 scopus 로고    scopus 로고
    • Rh(I)-Catalyzed asymmetric intramolecular Pauson-Khand reaction in aqueous media
    • Suh WH, Choi M, Lee SI, Chung YK (2003) Rh(I)-Catalyzed asymmetric intramolecular Pauson-Khand reaction in aqueous media. Synthesis 2003:2169-2172.
    • (2003) Synthesis , vol.2003 , pp. 2169-2172
    • Suh, W.H.1    Choi, M.2    Lee, S.I.3    Chung, Y.K.4
  • 36
    • 0035840386 scopus 로고    scopus 로고
    • Solid-phase synthesis of isoindolines via a rhodium-catalyzed [2 + 2 + 2] cycloaddition
    • Sun Q, Zhou XM, Islam K, Kyle DJ (2001) Solid-phase synthesis of isoindolines via a rhodium-catalyzed [2 + 2 + 2] cycloaddition. Tetrahedron Lett 42:6495-6497.
    • (2001) Tetrahedron Lett , vol.42 , pp. 6495-6497
    • Sun, Q.1    Zhou, X.M.2    Islam, K.3    Kyle, D.J.4
  • 37
    • 33746277260 scopus 로고    scopus 로고
    • Solid-supported [2 + 2 + 2] cyclotrimerizations
    • Young DD, Senaiar RS, Deiters A (2006) Solid-supported [2 + 2 + 2] cyclotrimerizations. Chem-Eur J 12:5563-5568.
    • (2006) Chem-Eur J , vol.12 , pp. 5563-5568
    • Young, D.D.1    Senaiar, R.S.2    Deiters, A.3
  • 38
    • 34848908965 scopus 로고    scopus 로고
    • Synthesis of indanones via solid-supported [2 + 2 + 2] cyclotrimerization
    • Senaiar RS, Teske JA, Young DD, Deiters A (2007) Synthesis of indanones via solid-supported [2 + 2 + 2] cyclotrimerization. J Org Chem 72:7801-7804.
    • (2007) J Org Chem , vol.72 , pp. 7801-7804
    • Senaiar, R.S.1    Teske, J.A.2    Young, D.D.3    Deiters, A.4
  • 39
    • 0034619173 scopus 로고    scopus 로고
    • Chemo- and regioselective crossed alkyne cyclotrimerisation of 1,6-diynes with terminal monoalkynes mediated by Grubbs' catalyst or Wilkinson's catalyst
    • Witulski B, Stengel T, Fernández-Hernández JM (2000) Chemo- and regioselective crossed alkyne cyclotrimerisation of 1,6-diynes with terminal monoalkynes mediated by Grubbs' catalyst or Wilkinson's catalyst. Chem Commun 1965-1966.
    • (2000) Chem Commun , pp. 1965-1966
    • Witulski, B.1    Stengel, T.2    Fernández-Hernández, J.M.3
  • 40
    • 77953299014 scopus 로고    scopus 로고
    • Synthesis and applications of tert-butanesulfinamide
    • Robak MT, Herbage MA, Ellman JA (2010) Synthesis and applications of tert-butanesulfinamide. Chem Rev 110:3600-3740.
    • (2010) Chem Rev , vol.110 , pp. 3600-3740
    • Robak, M.T.1    Herbage, M.A.2    Ellman, J.A.3
  • 41
    • 0038512037 scopus 로고    scopus 로고
    • Molecular shape diversity of combinatorial libraries: A prerequisite for broad bioactivity
    • Sauer WHB, Schwarz MK (2003) Molecular shape diversity of combinatorial libraries: A prerequisite for broad bioactivity. J Chem Inf Comput Sci 43:987-1003.
    • (2003) J Chem Inf Comput Sci , vol.43 , pp. 987-1003
    • Sauer, W.H.B.1    Schwarz, M.K.2
  • 42
    • 77952552641 scopus 로고    scopus 로고
    • Cheminformatics approaches to analyze diversity in compound screening libraries
    • Akella LB, DeCaprio D (2010) Cheminformatics approaches to analyze diversity in compound screening libraries. Curr Opin Chem Biol 14:325-330.
    • (2010) Curr Opin Chem Biol , vol.14 , pp. 325-330
    • Akella, L.B.1    DeCaprio, D.2
  • 43
    • 78649527328 scopus 로고    scopus 로고
    • An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: Discovery of macrocyclic histone deacetylase inhibitors
    • Marcaurelle LA, et al. (2010) An aldol-based build/couple/pair strategy for the synthesis of medium- and large-sized rings: Discovery of macrocyclic histone deacetylase inhibitors. J Am Chem Soc 132:16962-16976.
    • (2010) J Am Chem Soc , vol.132 , pp. 16962-16976
    • Marcaurelle, L.A.1
  • 44
    • 77953592675 scopus 로고    scopus 로고
    • Stereochemical and skeletal diversity arising from amino propargylic alcohols
    • Pizzirani D, Kaya T, Clemons PA, Schreiber SL (2010) Stereochemical and skeletal diversity arising from amino propargylic alcohols. Org Lett 12:2822-2825.
    • (2010) Org Lett , vol.12 , pp. 2822-2825
    • Pizzirani, D.1    Kaya, T.2    Clemons, P.A.3    Schreiber, S.L.4
  • 45
    • 77951133670 scopus 로고    scopus 로고
    • Reagent based DOS: A "Click, Click, Cyclize" strategy to probe chemical space
    • Rolfe A, Lushington GH, Hanson PR (2010) Reagent based DOS: A "Click, Click, Cyclize" strategy to probe chemical space. Org Biomol Chem 8:2198-2203.
    • (2010) Org Biomol Chem , vol.8 , pp. 2198-2203
    • Rolfe, A.1    Lushington, G.H.2    Hanson, P.R.3


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