메뉴 건너뛰기




Volumn 7, Issue 4, 2009, Pages 705-753

A submarine journey: The pyrrole-imidazole alkaloids

Author keywords

Marine sponges; Oroidin; Pyrrole imidazole alkaloids; Total synthesis

Indexed keywords

2 DEBROMOHYMENIALDISINE; AGELADINE A; AGELASTATIN A; AGELASTATIN B; AGELASTATIN C; AGELASTATIN D; AGELIFERIN; ALKALOID DERIVATIVE; AXINELLAMINE; AXINOHYDANTOIN; DEBROMOAXINOHYDANTOIN; DIBROMOPHAKELLIN; DIBROMOPHAKELLSTATIN; DIBROMOSIOPHAKELLIN; DISPACAMIDE A; HYMENIALDISINE; HYMENIDIN; IMIDAZOLE DERIVATIVE; MASSADINE; NAGELAMIDE D; OROIDIN; PALAU'AMINE; PYRROLE DERIVATIVE; SCEPTRIN; STYLISSADINE A; STYLISSADINE B; UNCLASSIFIED DRUG; VERPACAMIDE C;

EID: 75149118318     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md7040705     Document Type: Review
Times cited : (218)

References (184)
  • 2
    • 0141742509 scopus 로고    scopus 로고
    • Synthesis of the pyrrole-imidazole alkaloids
    • Hoffmann, H.; Lindel, T. Synthesis of the pyrrole-imidazole alkaloids. Synthesis 2003, 1753-1783.
    • (2003) Synthesis , pp. 1753-1783
    • Hoffmann, H.1    Lindel, T.2
  • 3
    • 24644462320 scopus 로고    scopus 로고
    • Challenge palau'amine: Current standings
    • Jacquot, D.E.N.; Lindel, T. Challenge palau'amine: Current standings. Curr. Org. Chem. 2005, 9, 1551-1565.
    • (2005) Curr. Org. Chem , vol.9 , pp. 1551-1565
    • Jacquot, D.E.N.1    Lindel, T.2
  • 4
    • 17844373306 scopus 로고    scopus 로고
    • Muscarine, imidazole, oxazole, and thiazole alkaloids
    • Jin, Z. Muscarine, imidazole, oxazole, and thiazole alkaloids. Nat. Prod. Rep. 2005, 22, 196-229.
    • (2005) Nat. Prod. Rep , vol.22 , pp. 196-229
    • Jin, Z.1
  • 5
    • 33744958901 scopus 로고    scopus 로고
    • Imidazole, oxazole and thiazole alkaloids
    • Jin, Z. Imidazole, oxazole and thiazole alkaloids. Nat. Prod. Rep. 2006, 23, 464-496.
    • (2006) Nat. Prod. Rep , vol.23 , pp. 464-496
    • Jin, Z.1
  • 6
    • 34249101573 scopus 로고    scopus 로고
    • Enzyme inhibitors from marine invertebrates
    • Nakao, Y.; Fusetani, N. Enzyme inhibitors from marine invertebrates. J. Nat. Prod. 2007, 70, 689-710.
    • (2007) J. Nat. Prod , vol.70 , pp. 689-710
    • Nakao, Y.1    Fusetani, N.2
  • 7
    • 34848832308 scopus 로고    scopus 로고
    • Some recent advances in the synthesis of polycyclic imidazole-containing marine natural products
    • Weinreb, S.M. Some recent advances in the synthesis of polycyclic imidazole-containing marine natural products. Nat. Prod. Rep. 2007, 24, 931-948.
    • (2007) Nat. Prod. Rep , vol.24 , pp. 931-948
    • Weinreb, S.M.1
  • 8
    • 59349102368 scopus 로고    scopus 로고
    • Marine natural products: Synthetic aspects
    • Morris, J.C.; Phillips, A.J. Marine natural products: Synthetic aspects. Nat. Prod. Rep. 2009, 26, 245-265.
    • (2009) Nat. Prod. Rep , vol.26 , pp. 245-265
    • Morris, J.C.1    Phillips, A.J.2
  • 10
    • 61449199502 scopus 로고    scopus 로고
    • Muscarine, imidazole, oxazole and thiazole alkaloids
    • Jin, Z. Muscarine, imidazole, oxazole and thiazole alkaloids. Nat. Prod. Rep. 2009, 26, 382-445.
    • (2009) Nat. Prod. Rep , vol.26 , pp. 382-445
    • Jin, Z.1
  • 11
    • 85008131292 scopus 로고
    • Marine natural products. XII. On the chemical constituents of the Okinawan marine sponge Hymeniacidon aldis
    • Kitagawa, I.; Kobayashi, M.; Kitanaka, K.; Kido, M.; Kyogoku, Y. Marine natural products. XII. On the chemical constituents of the Okinawan marine sponge Hymeniacidon aldis. Chem. Pharm. Bull. 1983, 31, 2321-2328.
    • (1983) Chem. Pharm. Bull , vol.31 , pp. 2321-2328
    • Kitagawa, I.1    Kobayashi, M.2    Kitanaka, K.3    Kido, M.4    Kyogoku, Y.5
  • 14
    • 0033603312 scopus 로고    scopus 로고
    • Biosynthetic studies of the alkaloid, stevensine, in a cell culture of the marine sponge Teichaxinella morchella
    • Andrade, P.; Willoughby, R.; Pomponi, S.A.; Kerr, R.G. Biosynthetic studies of the alkaloid, stevensine, in a cell culture of the marine sponge Teichaxinella morchella. Tetrahedron Lett. 1999, 40, 4775-4778.
    • (1999) Tetrahedron Lett , vol.40 , pp. 4775-4778
    • Andrade, P.1    Willoughby, R.2    Pomponi, S.A.3    Kerr, R.G.4
  • 15
    • 0000933149 scopus 로고    scopus 로고
    • New bromopyrrole alkaloid from the marine sponge Agelas wiedenmeyeri
    • Assmann, M.; Lichte, E.; Van Soest, R.W.M.; Köck, M. New bromopyrrole alkaloid from the marine sponge Agelas wiedenmeyeri. Org. Lett. 1999, 1, 455-457.
    • (1999) Org. Lett , vol.1 , pp. 455-457
    • Assmann, M.1    Lichte, E.2    Van Soest, R.W.M.3    Köck, M.4
  • 16
    • 33745711792 scopus 로고    scopus 로고
    • 5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: Possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids. Org. Lett. 2006, 8, 2421-2424.
    • 5 diketopiperazines relating cyclo(Pro-Pro) to cyclo(Pro-Arg), from the marine sponge Axinella vaceleti: Possible biogenetic precursors of pyrrole-2-aminoimidazole alkaloids. Org. Lett. 2006, 8, 2421-2424.
  • 17
    • 4143115664 scopus 로고    scopus 로고
    • A likely biogenetic gateway linking 2-aminoimidazolinone metabolites of sponges to proline: Spontaneous oxidative conversion of the pyrrole-proline-guanidine pseudo-peptide to dispacamide A
    • Travert, N.; Al Mourabit, A. A likely biogenetic gateway linking 2-aminoimidazolinone metabolites of sponges to proline: Spontaneous oxidative conversion of the pyrrole-proline-guanidine pseudo-peptide to dispacamide A. J. Am. Chem. Soc. 2004, 126, 10252-10253.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 10252-10253
    • Travert, N.1    Al Mourabit, A.2
  • 18
    • 0000189135 scopus 로고
    • Biomimetic synthesis of dibromophakellin
    • Foley, L.H.; Büchi, G. Biomimetic synthesis of dibromophakellin. J. Am. Chem. Soc. 1982, 104, 1776-1777.
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 1776-1777
    • Foley, L.H.1    Büchi, G.2
  • 19
    • 0000784643 scopus 로고
    • The structure of dibromoagelaspongin - A novel bromine-containing guanidine derivative from the marine sponge Agelas sp
    • Fedoreev, S.A.; Il'In, S.G.; Utkina, N.K.; Maksimov, O.B.; Reshetnyak, M.V.; Antipin, M.Y.; Struchkov, Y.T. The structure of dibromoagelaspongin - A novel bromine-containing guanidine derivative from the marine sponge Agelas sp. Tetrahedron 1989, 45, 3487-3492.
    • (1989) Tetrahedron , vol.45 , pp. 3487-3492
    • Fedoreev, S.A.1    Il'In, S.G.2    Utkina, N.K.3    Maksimov, O.B.4    Reshetnyak, M.V.5    Antipin, M.Y.6    Struchkov, Y.T.7
  • 20
    • 0027170397 scopus 로고    scopus 로고
    • D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. Agelastatin A, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the Coral sea. J. Chem. Soc., Chem. Commun. 1993, 1305-1306.
    • D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. Agelastatin A, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the Coral sea. J. Chem. Soc., Chem. Commun. 1993, 1305-1306.
  • 21
    • 0029956189 scopus 로고    scopus 로고
    • Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Mauritiamine, a new antifouling oroidin dimer from the marine sponge Agelas mauritiana. J. Nat. Prod. 1996, 59, 501-503.
    • Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. Mauritiamine, a new antifouling oroidin dimer from the marine sponge Agelas mauritiana. J. Nat. Prod. 1996, 59, 501-503.
  • 23
    • 13444252897 scopus 로고    scopus 로고
    • Spirocycloisomerization of tethered alkylidene glycocyamidines: Synthesis of a base template common to the palau'amine family of alkaloids
    • Garrido-Hernandez, H.; Nakadai, M.; Vimolratana, M.; Li, Q.; Doundoulakis, T.; Harran, P.G. Spirocycloisomerization of tethered alkylidene glycocyamidines: Synthesis of a base template common to the palau'amine family of alkaloids. Angew. Chem., Int. Ed. 2005, 44, 765-769.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 765-769
    • Garrido-Hernandez, H.1    Nakadai, M.2    Vimolratana, M.3    Li, Q.4    Doundoulakis, T.5    Harran, P.G.6
  • 24
    • 70449448431 scopus 로고
    • Natural products chemistry of the marine environment
    • Faulkner, D.J.; Andersen, R.J. Natural products chemistry of the marine environment. Sea 1974, 5, 679-714.
    • (1974) Sea , vol.5 , pp. 679-714
    • Faulkner, D.J.1    Andersen, R.J.2
  • 25
    • 0017571638 scopus 로고
    • Natural products of marine sponges. 7. The constitution of weakly basic guanidine compounds, dibromophakellin and monobromophakellin
    • Sharma, G.; Magdoff-Fairchild, B. Natural products of marine sponges. 7. The constitution of weakly basic guanidine compounds, dibromophakellin and monobromophakellin. J. Org. Chem. 1977, 42, 4118-4124.
    • (1977) J. Org. Chem , vol.42 , pp. 4118-4124
    • Sharma, G.1    Magdoff-Fairchild, B.2
  • 26
    • 2942673078 scopus 로고    scopus 로고
    • Natural product synthesis: Sceptrin as a potential biosynthetic precursor to complex pyrrole-imidazole alkaloids: The total synthesis of ageliferin
    • Baran, P.S.; O'Malley, D.P.; Zografos, A.L. Natural product synthesis: Sceptrin as a potential biosynthetic precursor to complex pyrrole-imidazole alkaloids: The total synthesis of ageliferin. Angew. Chem., Int. Ed. 2004, 43, 2674-2677.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 2674-2677
    • Baran, P.S.1    O'Malley, D.P.2    Zografos, A.L.3
  • 27
    • 33744980982 scopus 로고    scopus 로고
    • Planned and unplanned halogenations in route to selected oroidin alkaloids
    • Wang, S.; Dilley, A.S.; Poullennec, K.G.; Romo, D. Planned and unplanned halogenations in route to selected oroidin alkaloids. Tetrahedron 2006, 62, 7155-7161.
    • (2006) Tetrahedron , vol.62 , pp. 7155-7161
    • Wang, S.1    Dilley, A.S.2    Poullennec, K.G.3    Romo, D.4
  • 28
    • 34548637762 scopus 로고    scopus 로고
    • Massadine chloride: A biosynthetic precursor of massadine and stylissadine
    • Grube, A.; Immel, S.; Baran, P.S.; Köck, M. Massadine chloride: A biosynthetic precursor of massadine and stylissadine. Angew. Chem., Int. Ed. 2007, 46, 6721-6724.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 6721-6724
    • Grube, A.1    Immel, S.2    Baran, P.S.3    Köck, M.4
  • 29
    • 0035136516 scopus 로고    scopus 로고
    • Potier, P. Sponge's molecular diversity through the ambivalent reactivity of 2-aminoimidazole: A universal chemical pathway to the oroidin-based pyrrole-imidazole alkaloids and their palau'amine congeners
    • Al Mourabit, A.; Potier, P. Sponge's molecular diversity through the ambivalent reactivity of 2-aminoimidazole: A universal chemical pathway to the oroidin-based pyrrole-imidazole alkaloids and their palau'amine congeners. Eur. J. Org. Chem. 2001, 237-243.
    • (2001) Eur. J. Org. Chem , pp. 237-243
    • Al Mourabit, A.1
  • 31
    • 0035035061 scopus 로고    scopus 로고
    • Microbial biosynthesis of halometabolites
    • Van Pee, K.-H. Microbial biosynthesis of halometabolites. Arch. Microbiol. 2001, 175, 250-258.
    • (2001) Arch. Microbiol , vol.175 , pp. 250-258
    • Van Pee, K.-H.1
  • 32
    • 1342290169 scopus 로고    scopus 로고
    • The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products
    • Butler, A.; Carter-Franklin, J.N. The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products. Nat. Prod. Rep. 2004, 21, 180-188.
    • (2004) Nat. Prod. Rep , vol.21 , pp. 180-188
    • Butler, A.1    Carter-Franklin, J.N.2
  • 33
    • 25844517049 scopus 로고    scopus 로고
    • Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination
    • Dong, C.; Flecks, S.; Unversucht, S.; Haupt, C.; van Pee, K.-H.; Naismith, J.H. Tryptophan 7-halogenase (PrnA) structure suggests a mechanism for regioselective chlorination. Science 2005, 309, 2216-2219.
    • (2005) Science , vol.309 , pp. 2216-2219
    • Dong, C.1    Flecks, S.2    Unversucht, S.3    Haupt, C.4    van Pee, K.-H.5    Naismith, J.H.6
  • 34
    • 0141518579 scopus 로고    scopus 로고
    • Nishimura, S.; Matsunaga, S.; Shibazaki, M.; Suzuki, K.; Furihata, K.; Van Soest, R.W.M.; Fusetani, N. Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa. Org. Lett. 2003, 5, 2255-2257.
    • Nishimura, S.; Matsunaga, S.; Shibazaki, M.; Suzuki, K.; Furihata, K.; Van Soest, R.W.M.; Fusetani, N. Massadine, a novel geranylgeranyltransferase type I inhibitor from the marine sponge Stylissa aff. massa. Org. Lett. 2003, 5, 2255-2257.
  • 35
    • 1642368422 scopus 로고    scopus 로고
    • Chiroptical analysis of marine sponge alkaloids sharing the pyrrolopyrazinone core
    • Jacquot, D.E.N.; Mayer, P.; Lindel, T. Chiroptical analysis of marine sponge alkaloids sharing the pyrrolopyrazinone core. Chem. Eur. J. 2004, 10, 1141-1148.
    • (2004) Chem. Eur. J , vol.10 , pp. 1141-1148
    • Jacquot, D.E.N.1    Mayer, P.2    Lindel, T.3
  • 36
    • 0034627361 scopus 로고    scopus 로고
    • Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides
    • Fattorusso, E.; Taglialatela-Scafati, O. Two novel pyrrole-imidazole alkaloids from the Mediterranean sponge Agelas oroides. Tetrahedron Lett. 2000, 41, 9917-9922.
    • (2000) Tetrahedron Lett , vol.41 , pp. 9917-9922
    • Fattorusso, E.1    Taglialatela-Scafati, O.2
  • 37
    • 0029904176 scopus 로고    scopus 로고
    • The active centers of agelastatin A, a strongly cytotoxic alkaloid of the Coral Sea axinellid sponge Agelas dendromorpha, as determined by comparative bioassays with semisynthetic derivatives
    • D'Ambrosio, M.; Guerriero, A.; Ripamonti, M.; Debitus, C.; Waikedre, J.; Pietra, F. The active centers of agelastatin A, a strongly cytotoxic alkaloid of the Coral Sea axinellid sponge Agelas dendromorpha, as determined by comparative bioassays with semisynthetic derivatives. Helv. Chim. Acta 1996, 79, 727-735.
    • (1996) Helv. Chim. Acta , vol.79 , pp. 727-735
    • D'Ambrosio, M.1    Guerriero, A.2    Ripamonti, M.3    Debitus, C.4    Waikedre, J.5    Pietra, F.6
  • 38
    • 0030621012 scopus 로고    scopus 로고
    • Chemical defense of the Caribbean sponge Agelas clathrodes (Schmidt)
    • Chanas, B.; Pawlik, J.R.; Lindel, T.; Fenical, W. Chemical defense of the Caribbean sponge Agelas clathrodes (Schmidt). J. Exp. Mar. Biol. Ecol. 1997, 208, 185-196.
    • (1997) J. Exp. Mar. Biol. Ecol , vol.208 , pp. 185-196
    • Chanas, B.1    Pawlik, J.R.2    Lindel, T.3    Fenical, W.4
  • 39
    • 0032760487 scopus 로고    scopus 로고
    • Chemical defense of the Caribbean reef sponge Axinella corrugata against predatory fishes
    • Wilson, D.M.; Puyana, M.; Fenical, W.; Pawlik, J.R. Chemical defense of the Caribbean reef sponge Axinella corrugata against predatory fishes. J. Chem. Ecol. 1999, 25, 2811-2823.
    • (1999) J. Chem. Ecol , vol.25 , pp. 2811-2823
    • Wilson, D.M.1    Puyana, M.2    Fenical, W.3    Pawlik, J.R.4
  • 40
    • 0033917903 scopus 로고    scopus 로고
    • Structure-activity relationship of inhibition of fish feeding by sponge-derived and synthetic pyrrole-imidazole alkaloids
    • Lindel, T.; Hoffmann, H.; Hochgurtel, M.; Pawlik, J.R. Structure-activity relationship of inhibition of fish feeding by sponge-derived and synthetic pyrrole-imidazole alkaloids. J. Chem. Ecol. 2000, 26, 1477-1496.
    • (2000) J. Chem. Ecol , vol.26 , pp. 1477-1496
    • Lindel, T.1    Hoffmann, H.2    Hochgurtel, M.3    Pawlik, J.R.4
  • 41
    • 0034763640 scopus 로고    scopus 로고
    • New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica
    • Assmann, M.; Van Soest, R.W.M.; Köck, M. New antifeedant bromopyrrole alkaloid from the Caribbean sponge Stylissa caribica. J. Nat. Prod. 2001, 64, 1345-1347.
    • (2001) J. Nat. Prod , vol.64 , pp. 1345-1347
    • Assmann, M.1    Van Soest, R.W.M.2    Köck, M.3
  • 42
    • 0034703772 scopus 로고    scopus 로고
    • Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera
    • Assmann, M.; Lichte, E.; Pawlik, J.R.; Köck, M. Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera. Mar. Ecol. Prog. Ser. 2000, 207, 255-262.
    • (2000) Mar. Ecol. Prog. Ser , vol.207 , pp. 255-262
    • Assmann, M.1    Lichte, E.2    Pawlik, J.R.3    Köck, M.4
  • 43
    • 3042681285 scopus 로고    scopus 로고
    • Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization- induced cellular calcium elevation
    • Bickmeyer, U.; Drechsler, C.; Köck, M.; Assmann, M. Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization- induced cellular calcium elevation. Toxicon 2004, 44, 45-51.
    • (2004) Toxicon , vol.44 , pp. 45-51
    • Bickmeyer, U.1    Drechsler, C.2    Köck, M.3    Assmann, M.4
  • 44
    • 15044362347 scopus 로고    scopus 로고
    • secondary metabolites from the marine sponge Agelas conifera, inhibit voltage-operated, but not store-operated calcium entry in PC12 cells
    • Bickmeyer, U. Bromoageliferin and dibromoageliferin, secondary metabolites from the marine sponge Agelas conifera, inhibit voltage-operated, but not store-operated calcium entry in PC12 cells. Toxicon 2005, 45, 627-632.
    • (2005) Toxicon , vol.45 , pp. 627-632
    • Bickmeyer1    Bromoageliferin, U.2    dibromoageliferin3
  • 45
    • 45949131479 scopus 로고
    • Marine invertebrates from the New Caledonian lagoon. V. Isolation and identification of metabolites of a new species of sponge, Pseudaxinyssa cantharella
    • De Nanteuil, G.; Ahond, A.; Guilhem, J.; Poupat, C.; Tran Huu Dau, E.; Potier, P.; Pusset, M.; Pusset, J.; Laboute, P. Marine invertebrates from the New Caledonian lagoon. V. Isolation and identification of metabolites of a new species of sponge, Pseudaxinyssa cantharella. Tetrahedron 1985, 41, 6019-6033.
    • (1985) Tetrahedron , vol.41 , pp. 6019-6033
    • De Nanteuil, G.1    Ahond, A.2    Guilhem, J.3    Poupat, C.4    Tran Huu Dau, E.5    Potier, P.6    Pusset, M.7    Pusset, J.8    Laboute, P.9
  • 47
    • 32644447581 scopus 로고
    • New bromopyrrole derivatives from the sponge Agelas oroides
    • Forenza, S.; Minale, L.; Riccio, R.; Fattorusso, E. New bromopyrrole derivatives from the sponge Agelas oroides. J. Chem. Soc. D. 1971, 1129-1130.
    • (1971) J. Chem. Soc. D , pp. 1129-1130
    • Forenza, S.1    Minale, L.2    Riccio, R.3    Fattorusso, E.4
  • 49
    • 0030961405 scopus 로고    scopus 로고
    • Synthesis of marine 2-aminoimidazole metabolites: Hymenidin, oroidin, and keramadine
    • Daninos-Zeghal, S.; Al Mourabit, A.; Ahond, A.; Poupat, C.; Potier, P. Synthesis of marine 2-aminoimidazole metabolites: Hymenidin, oroidin, and keramadine. Tetrahedron 1997, 53, 7605-7614.
    • (1997) Tetrahedron , vol.53 , pp. 7605-7614
    • Daninos-Zeghal, S.1    Al Mourabit, A.2    Ahond, A.3    Poupat, C.4    Potier, P.5
  • 50
    • 0037043013 scopus 로고    scopus 로고
    • Synthesis of the marine sponge alkaloid oroidin and its analogues via Suzuki cross-coupling reactions
    • Berree, F.; Girard-Le Bleis, P.; Carboni, B. Synthesis of the marine sponge alkaloid oroidin and its analogues via Suzuki cross-coupling reactions. Tetrahedron Lett. 2002, 43, 4935-4938.
    • (2002) Tetrahedron Lett , vol.43 , pp. 4935-4938
    • Berree, F.1    Girard-Le Bleis, P.2    Carboni, B.3
  • 51
    • 0001208852 scopus 로고    scopus 로고
    • 5 marine alkaloids oroidin, clathrodin, and dispacamides. Preparation and transformation of 2-amino-4,5-dialkoxy-4,5- dihydroimidazoline from 2-aminoimidazoles
    • 5 marine alkaloids oroidin, clathrodin, and dispacamides. Preparation and transformation of 2-amino-4,5-dialkoxy-4,5- dihydroimidazoline from 2-aminoimidazoles. J. Org. Chem. 1998, 63, 1248-1253.
    • (1998) J. Org. Chem , vol.63 , pp. 1248-1253
    • Olofson, A.1    Yakushijin, K.2    Horne, D.A.3
  • 52
    • 0028600543 scopus 로고
    • A simple and practical synthesis of 2-aminoimidazoles
    • Little, T.L.; Webber, S.E. A simple and practical synthesis of 2-aminoimidazoles. J. Org. Chem. 1994, 59, 7299-7305.
    • (1994) J. Org. Chem , vol.59 , pp. 7299-7305
    • Little, T.L.1    Webber, S.E.2
  • 53
    • 33750511308 scopus 로고    scopus 로고
    • A novel synthesis of the 2-aminoimidazol-4- carbaldehyde derivatives, versatile synthetic intermediates for 2-aminoimidazole alkaloids
    • Ando, N.; Terashima, S. A novel synthesis of the 2-aminoimidazol-4- carbaldehyde derivatives, versatile synthetic intermediates for 2-aminoimidazole alkaloids. Synlett 2006, 2836-2840.
    • (2006) Synlett , pp. 2836-2840
    • Ando, N.1    Terashima, S.2
  • 54
    • 33746654160 scopus 로고    scopus 로고
    • Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridine intermediates
    • Schroif-Gregoire, C.; Travert, N.; Zaparucha, A.; Al Mourabit, A. Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridine intermediates. Org. Lett. 2006, 8, 2961-2964.
    • (2006) Org. Lett , vol.8 , pp. 2961-2964
    • Schroif-Gregoire, C.1    Travert, N.2    Zaparucha, A.3    Al Mourabit, A.4
  • 57
    • 0036228505 scopus 로고    scopus 로고
    • Biofilms: Survival mechanisms of clinically relevant microorganisms
    • Donlan, R.M.; Costerton, J.W. Biofilms: Survival mechanisms of clinically relevant microorganisms. Clin. Microbiol. Rev. 2002, 15, 167-193.
    • (2002) Clin. Microbiol. Rev , vol.15 , pp. 167-193
    • Donlan, R.M.1    Costerton, J.W.2
  • 58
    • 33746521142 scopus 로고    scopus 로고
    • Chemical countermeasures for the control of bacterial biofilms: Effective compounds and promising targets
    • Musk, D.J., Jr.; Hergenrother, P.J. Chemical countermeasures for the control of bacterial biofilms: Effective compounds and promising targets. Curr. Med. Chem. 2006, 13, 2163-2177.
    • (2006) Curr. Med. Chem , vol.13 , pp. 2163-2177
    • Musk Jr., D.J.1    Hergenrother, P.J.2
  • 60
    • 41549147302 scopus 로고    scopus 로고
    • Inhibition and dispersion of Pseudomonas aeruginosa biofilms with reverse amide 2-aminoimidazole oroidin analogs
    • Richards, J.J.; Ballard, T.E.; Melander, C. Inhibition and dispersion of Pseudomonas aeruginosa biofilms with reverse amide 2-aminoimidazole oroidin analogs. Org. Biomol. Chem. 2008, 6, 1356-1363.
    • (2008) Org. Biomol. Chem , vol.6 , pp. 1356-1363
    • Richards, J.J.1    Ballard, T.E.2    Melander, C.3
  • 61
    • 56749131234 scopus 로고    scopus 로고
    • Synthesis and antibiofilm activity of a second-generation reverse-amide oroidin library: A structure-activity relationship study
    • Ballard, T.E.; Richards, J.J.; Wolfe, A.L.; Melander, C. Synthesis and antibiofilm activity of a second-generation reverse-amide oroidin library: A structure-activity relationship study. Chem. Eur. J. 2008, 14, 10745-10761.
    • (2008) Chem. Eur. J , vol.14 , pp. 10745-10761
    • Ballard, T.E.1    Richards, J.J.2    Wolfe, A.L.3    Melander, C.4
  • 62
    • 47749136945 scopus 로고    scopus 로고
    • Effects of N-pyrrole substitution on the anti-biofilm activities of oroidin derivatives against Acinetobacter baumannii
    • Richards, J.J.; Reed, C.S.; Melander, C. Effects of N-pyrrole substitution on the anti-biofilm activities of oroidin derivatives against Acinetobacter baumannii. Bioorg. Med. Chem. Lett. 2008, 18, 4325-4327.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 4325-4327
    • Richards, J.J.1    Reed, C.S.2    Melander, C.3
  • 64
    • 49249135187 scopus 로고    scopus 로고
    • Synthesis and screening of an oroidin library against Pseudomonas aeruginosa biofilms
    • Richards, J.J.; Ballard, T.E.; Huigens, R.W. III; Melander, C. Synthesis and screening of an oroidin library against Pseudomonas aeruginosa biofilms. ChemBioChem. 2008, 9, 1267-1279.
    • (2008) ChemBioChem , vol.9 , pp. 1267-1279
    • Richards, J.J.1    Ballard, T.E.2    Huigens III, R.W.3    Melander, C.4
  • 66
    • 0030833160 scopus 로고    scopus 로고
    • Synthesis of dispacamide from the marine sponge Agelas dispar
    • Lindel, T.; Hoffmann, H. Synthesis of dispacamide from the marine sponge Agelas dispar. Tetrahedron Lett. 1997, 38, 8935-8938.
    • (1997) Tetrahedron Lett , vol.38 , pp. 8935-8938
    • Lindel, T.1    Hoffmann, H.2
  • 67
    • 0035966623 scopus 로고    scopus 로고
    • A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids
    • Fresneda, P.M.; Molina, P.; Sanz, M.A. A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids. Tetrahedron Lett. 2001, 42, 851-854.
    • (2001) Tetrahedron Lett , vol.42 , pp. 851-854
    • Fresneda, P.M.1    Molina, P.2    Sanz, M.A.3
  • 69
    • 70350738510 scopus 로고    scopus 로고
    • Preparation of hymenialdisine, analogues and their evaluation as kinase inhibitors
    • Nguyen, T.N.T.; Tepe, J.J. Preparation of hymenialdisine, analogues and their evaluation as kinase inhibitors. Curr. Med. Chem. 2009, 16, 3122-3143.
    • (2009) Curr. Med. Chem , vol.16 , pp. 3122-3143
    • Nguyen, T.N.T.1    Tepe, J.J.2
  • 70
    • 37049104733 scopus 로고
    • Characterization of a yellow compound isolated from the marine sponge Phakellia flabellata
    • Sharma, G.M.; Buyer, J.S.; Pomerantz, M.W. Characterization of a yellow compound isolated from the marine sponge Phakellia flabellata. J. Chem. Soc., Chem. Commun. 1980, 435-436.
    • (1980) J. Chem. Soc., Chem. Commun , pp. 435-436
    • Sharma, G.M.1    Buyer, J.S.2    Pomerantz, M.W.3
  • 71
  • 72
    • 0039430353 scopus 로고
    • 4-(2-Amino-4-oxo-2-imidazolin-5- ylidene)-2-bromo-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one methanol solvate: A new bromo compound from the sponge Acanthella Aurantiaca
    • Mattia, C.A.; Mazzarella, L.; Puliti, R. 4-(2-Amino-4-oxo-2-imidazolin-5- ylidene)-2-bromo-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one methanol solvate: A new bromo compound from the sponge Acanthella Aurantiaca. Acta Crystallogr., Sect. B 1982, B38, 2513-2515.
    • (1982) Acta Crystallogr., Sect. B , vol.B38 , pp. 2513-2515
    • Mattia, C.A.1    Mazzarella, L.2    Puliti, R.3
  • 73
    • 10544237275 scopus 로고    scopus 로고
    • Isomers and tautomers of hymenialdisine and debromohymenialdisine
    • Williams, D.H.; Faulkner, D.J. Isomers and tautomers of hymenialdisine and debromohymenialdisine. Nat. Prod. Lett. 1996, 9, 57-64.
    • (1996) Nat. Prod. Lett , vol.9 , pp. 57-64
    • Williams, D.H.1    Faulkner, D.J.2
  • 74
    • 0028801824 scopus 로고
    • Total syntheses of hymenialdisine and debromohymenialdisine: Stereospecific construction of the 2-amino-4-oxo-2- imidazolin-5(Z)-disubstituted ylidene ring system
    • Annoura, H.; Tatsuoka, T. Total syntheses of hymenialdisine and debromohymenialdisine: Stereospecific construction of the 2-amino-4-oxo-2- imidazolin-5(Z)-disubstituted ylidene ring system. Tetrahedron Lett. 1995, 36, 413-416.
    • (1995) Tetrahedron Lett , vol.36 , pp. 413-416
    • Annoura, H.1    Tatsuoka, T.2
  • 75
    • 0031019028 scopus 로고    scopus 로고
    • 5 marine sponge alkaloids: (±)-Hymenin, stevensine, hymenialdisine, and debromohymenialdisine
    • 5 marine sponge alkaloids: (±)-Hymenin, stevensine, hymenialdisine, and debromohymenialdisine. J. Org. Chem. 1997, 62, 456-464.
    • (1997) J. Org. Chem , vol.62 , pp. 456-464
    • Xu, Y.-Z.1    Yakushijin, K.2    Horne, D.A.3
  • 76
    • 0000072298 scopus 로고    scopus 로고
    • A practical synthesis of (Z)-debromohymenialdisine
    • Sosa, A.C.B.; Yakushijin, K.; Horne, D.A. A practical synthesis of (Z)-debromohymenialdisine. J. Org. Chem. 2000, 65, 610-611.
    • (2000) J. Org. Chem , vol.65 , pp. 610-611
    • Sosa, A.C.B.1    Yakushijin, K.2    Horne, D.A.3
  • 77
    • 0344441316 scopus 로고    scopus 로고
    • An expeditious multigram preparation of the marine protein kinase inhibitor debromohymenialdisine
    • Portevin, B.; Golsteyn, R.M.; Pierre, A.; De Nanteuil, G. An expeditious multigram preparation of the marine protein kinase inhibitor debromohymenialdisine. Tetrahedron Lett. 2003, 44, 9263-9265.
    • (2003) Tetrahedron Lett , vol.44 , pp. 9263-9265
    • Portevin, B.1    Golsteyn, R.M.2    Pierre, A.3    De Nanteuil, G.4
  • 78
    • 29444445314 scopus 로고    scopus 로고
    • A new glycocyamidine ring precursor: Syntheses of (Z)-hymenialdisine, (Z)-2- debromohymenialdisine, and (±)-endo-2-debromohymenialdisine
    • Papeo, G.; Posteri, H.; Borghi, D.; Varasi, M. A new glycocyamidine ring precursor: Syntheses of (Z)-hymenialdisine, (Z)-2- debromohymenialdisine, and (±)-endo-2-debromohymenialdisine. Org. Lett. 2005, 7, 5641-5644.
    • (2005) Org. Lett , vol.7 , pp. 5641-5644
    • Papeo, G.1    Posteri, H.2    Borghi, D.3    Varasi, M.4
  • 79
    • 84961499829 scopus 로고
    • Pharmacologically active substances from southern pacific marine invertebrates
    • Endo, M.; Nakagawa, M.; Hamamoto, Y.; Ishihama, M. Pharmacologically active substances from southern pacific marine invertebrates. Pure Appl. Chem. 1986, 58, 387-394.
    • (1986) Pure Appl. Chem , vol.58 , pp. 387-394
    • Endo, M.1    Nakagawa, M.2    Hamamoto, Y.3    Ishihama, M.4
  • 80
    • 33846963807 scopus 로고    scopus 로고
    • Synthesis of 2-substituted endo-hymenialdisine derivatives
    • He, Q.; Chen, W.; Qin, Y. Synthesis of 2-substituted endo-hymenialdisine derivatives. Tetrahedron Lett. 2007, 48, 1899-1901.
    • (2007) Tetrahedron Lett , vol.48 , pp. 1899-1901
    • He, Q.1    Chen, W.2    Qin, Y.3
  • 81
    • 0034705460 scopus 로고    scopus 로고
    • Synthesis and reactivity of azepino[3,4-b]indol-5-yl trifluoromethanesulfonate
    • Chacun-Lefevre, L.; Joseph, B.; Merour, J.-Y. Synthesis and reactivity of azepino[3,4-b]indol-5-yl trifluoromethanesulfonate. Tetrahedron 2000, 56, 4491-4499.
    • (2000) Tetrahedron , vol.56 , pp. 4491-4499
    • Chacun-Lefevre, L.1    Joseph, B.2    Merour, J.-Y.3
  • 82
    • 35948938476 scopus 로고    scopus 로고
    • Preparation of novel unsymmetrical bisindoles under solvent-free conditions: Synthesis, crystal structures, and mechanistic aspects
    • Kaiser, H.M.; Zenz, I.; Lo, W.F.; Spannenberg, A.; Schroeder, K.; Jiao, H.; Goerdes, D.; Beller, M.; Tse, M.K. Preparation of novel unsymmetrical bisindoles under solvent-free conditions: Synthesis, crystal structures, and mechanistic aspects. J. Org. Chem. 2007, 72, 8847-8858.
    • (2007) J. Org. Chem , vol.72 , pp. 8847-8858
    • Kaiser, H.M.1    Zenz, I.2    Lo, W.F.3    Spannenberg, A.4    Schroeder, K.5    Jiao, H.6    Goerdes, D.7    Beller, M.8    Tse, M.K.9
  • 83
    • 45449090011 scopus 로고    scopus 로고
    • Synthesis of novel hymenialdisine analogues using solvent-free and silica gel-promoted ring opening of epoxides
    • Mangu, N.; Kaiser, H.M.; Kar, A.; Spannenberg, A.; Beller, M.; Tse, M.K. Synthesis of novel hymenialdisine analogues using solvent-free and silica gel-promoted ring opening of epoxides. Tetrahedron 2008, 64, 7171-7177.
    • (2008) Tetrahedron , vol.64 , pp. 7171-7177
    • Mangu, N.1    Kaiser, H.M.2    Kar, A.3    Spannenberg, A.4    Beller, M.5    Tse, M.K.6
  • 86
    • 84988074643 scopus 로고
    • The isolation and structure elucidation of debromoaxinohydantoin
    • Groszek, G.; Kantoci, D.; Pettit, G.R. The isolation and structure elucidation of debromoaxinohydantoin. Liebigs Ann. 1995, 715-716.
    • (1995) Liebigs Ann , pp. 715-716
    • Groszek, G.1    Kantoci, D.2    Pettit, G.R.3
  • 87
    • 0030971562 scopus 로고    scopus 로고
    • Patil, A.D.; Freyer, A.J.; Killmer, L.; Hofmann, G.; Johnson, R.K. (Z)-Axinohydantoin and debromo-(Z)-axinohydantoin from the sponge Stylotella aurantium. Inhibitors of protein kinase C. Nat. Prod. Lett. 1997, 9, 201-207.
    • Patil, A.D.; Freyer, A.J.; Killmer, L.; Hofmann, G.; Johnson, R.K. (Z)-Axinohydantoin and debromo-(Z)-axinohydantoin from the sponge Stylotella aurantium. Inhibitors of protein kinase C. Nat. Prod. Lett. 1997, 9, 201-207.
  • 88
    • 0031775784 scopus 로고    scopus 로고
    • Spongiacidins A-D, new bromopyrrole alkaloids from Hymeniacidon sponge
    • Inaba, K.; Sato, H.; Tsuda, M.; Kobayashi, J.I. Spongiacidins A-D, new bromopyrrole alkaloids from Hymeniacidon sponge. J. Nat. Prod. 1998, 61, 693-695.
    • (1998) J. Nat. Prod , vol.61 , pp. 693-695
    • Inaba, K.1    Sato, H.2    Tsuda, M.3    Kobayashi, J.I.4
  • 90
  • 91
    • 0031019142 scopus 로고    scopus 로고
    • Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian Ocean sponge Phakellia mauritiana
    • Boyd, M.R.; Pettit, G.R.; McNulty, J.; Herald, D.L.; Doubek, D.L.; Chapuis, J.-C.; Schmidt, J.M.; Tackett, L.P. Antineoplastic agents. 362. Isolation and X-ray crystal structure of dibromophakellstatin from the Indian Ocean sponge Phakellia mauritiana. J. Nat. Prod. 1997, 60, 180-183.
    • (1997) J. Nat. Prod , vol.60 , pp. 180-183
    • Boyd, M.R.1    Pettit, G.R.2    McNulty, J.3    Herald, D.L.4    Doubek, D.L.5    Chapuis, J.-C.6    Schmidt, J.M.7    Tackett, L.P.8
  • 92
    • 17644414184 scopus 로고    scopus 로고
    • Total synthesis of the marine natural product racdibromophakellstatin
    • Jacquot, D.E.N.; Zoellinger, M.; Lindel, T. Total synthesis of the marine natural product racdibromophakellstatin. Angew. Chem., Int. Ed. 2005, 44, 2295-2298.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 2295-2298
    • Jacquot, D.E.N.1    Zoellinger, M.2    Lindel, T.3
  • 93
    • 33845528316 scopus 로고    scopus 로고
    • Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation
    • Zoellinger, M.; Mayer, P.; Lindel, T. Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation. J. Org. Chem. 2006, 71, 9431-9439.
    • (2006) J. Org. Chem , vol.71 , pp. 9431-9439
    • Zoellinger, M.1    Mayer, P.2    Lindel, T.3
  • 94
    • 15044360580 scopus 로고    scopus 로고
    • Extending Pummerer reaction chemistry. Synthesis of (±)-dibromophakellstatin by oxidative cyclization of an imidazole derivative
    • Feldman, K.S.; Skoumbourdis, A.P. Extending Pummerer reaction chemistry. Synthesis of (±)-dibromophakellstatin by oxidative cyclization of an imidazole derivative. Org. Lett. 2005, 7, 929-931.
    • (2005) Org. Lett , vol.7 , pp. 929-931
    • Feldman, K.S.1    Skoumbourdis, A.P.2
  • 95
    • 35348831073 scopus 로고    scopus 로고
    • Extending Pummerer reaction chemistry. Synthesis studies in the phakellin alkaloid area
    • Feldman, K.S.; Skoumbourdis, A.P.; Fodor, M.D. Extending Pummerer reaction chemistry. Synthesis studies in the phakellin alkaloid area. J. Org. Chem. 2007, 72, 8076-8086.
    • (2007) J. Org. Chem , vol.72 , pp. 8076-8086
    • Feldman, K.S.1    Skoumbourdis, A.P.2    Fodor, M.D.3
  • 96
    • 8744221400 scopus 로고    scopus 로고
    • Hypervalent iodine-mediated vicinal syn diazidation: Application to the total synthesis of (±)-dibromophakellstatin
    • Chung, R.; Yu, E.; Incarvito, C.D.; Austin, D.J. Hypervalent iodine-mediated vicinal syn diazidation: Application to the total synthesis of (±)-dibromophakellstatin. Org. Lett. 2004, 6, 3881-3884.
    • (2004) Org. Lett , vol.6 , pp. 3881-3884
    • Chung, R.1    Yu, E.2    Incarvito, C.D.3    Austin, D.J.4
  • 97
    • 34347214018 scopus 로고    scopus 로고
    • Palladium-catalyzed direct functionalization of imidazolinone: Synthesis of dibromophakellstatin
    • Lu, J.; Tan, X.; Chen, C. Palladium-catalyzed direct functionalization of imidazolinone: Synthesis of dibromophakellstatin. J. Am. Chem. Soc. 2007, 129, 7768-7769.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 7768-7769
    • Lu, J.1    Tan, X.2    Chen, C.3
  • 98
    • 35648950535 scopus 로고    scopus 로고
    • Enantioselective total synthesis of (-)-dibromophakellstatin
    • Zoellinger, M.; Mayer, P.; Lindel, T. Enantioselective total synthesis of (-)-dibromophakellstatin. Synlett 2007, 2756-2758.
    • (2007) Synlett , pp. 2756-2758
    • Zoellinger, M.1    Mayer, P.2    Lindel, T.3
  • 99
    • 33846047483 scopus 로고    scopus 로고
    • Antitumor activity of the marine natural product dibromophakellstatin in vitro
    • Zoellinger, M.; Kelter, G.; Fiebig, H.-H.; Lindel, T. Antitumor activity of the marine natural product dibromophakellstatin in vitro. Bioorg. Med. Chem. Lett. 2007, 17, 346-349.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 346-349
    • Zoellinger, M.1    Kelter, G.2    Fiebig, H.-H.3    Lindel, T.4
  • 100
    • 0028116772 scopus 로고
    • Conformational preferences and absolute configuration of agelastatin A, a cytotoxic alkaloid of the axinellid sponge Agelas dendromorpha from the Coral Sea, via combined molecular modeling, NMR, and exciton splitting for diamide and hydroxyamide derivatives
    • D'Ambrosio, M.; Guerriero, A.; Chiasera, G.; Pietra, F. Conformational preferences and absolute configuration of agelastatin A, a cytotoxic alkaloid of the axinellid sponge Agelas dendromorpha from the Coral Sea, via combined molecular modeling, NMR, and exciton splitting for diamide and hydroxyamide derivatives. Helv. Chim. Acta 1994, 77, 1895-1902.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 1895-1902
    • D'Ambrosio, M.1    Guerriero, A.2    Chiasera, G.3    Pietra, F.4
  • 101
    • 0031886176 scopus 로고    scopus 로고
    • Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A
    • Hong, T.W.; Jimenez, D.R.; Molinski, T.F. Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A. J. Nat. Prod. 1998, 61, 158-161.
    • (1998) J. Nat. Prod , vol.61 , pp. 158-161
    • Hong, T.W.1    Jimenez, D.R.2    Molinski, T.F.3
  • 102
    • 16344396159 scopus 로고    scopus 로고
    • Antineoplastic agents. 470. Absolute configuration of the marine sponge bromopyrrole agelastatin A
    • Pettit, G.R.; Ducki, S.; Herald, D.L.; Doubek, D.L.; Schmidt, J.M.; Chapuis, J.-C. Antineoplastic agents. 470. Absolute configuration of the marine sponge bromopyrrole agelastatin A. Oncol. Res. 2005, 15, 11-20.
    • (2005) Oncol. Res , vol.15 , pp. 11-20
    • Pettit, G.R.1    Ducki, S.2    Herald, D.L.3    Doubek, D.L.4    Schmidt, J.M.5    Chapuis, J.-C.6
  • 105
    • 13644254794 scopus 로고    scopus 로고
    • Molecular mechanisms of drug resistance
    • Longley, D.B.; Johnston, P.G. Molecular mechanisms of drug resistance. J. Pathol. 2005, 205, 275-292.
    • (2005) J. Pathol , vol.205 , pp. 275-292
    • Longley, D.B.1    Johnston, P.G.2
  • 106
    • 0141743548 scopus 로고    scopus 로고
    • Enantiospecific formal total synthesis of the tumor and GSK-3β inhibiting alkaloid, (-)-agelastatin A
    • Hale, K.J.; Domostoj, M.M.; Tocher, D.A.; Irving, E.; Scheinmann, F. Enantiospecific formal total synthesis of the tumor and GSK-3β inhibiting alkaloid, (-)-agelastatin A. Org. Lett. 2003, 5, 2927-2930.
    • (2003) Org. Lett , vol.5 , pp. 2927-2930
    • Hale, K.J.1    Domostoj, M.M.2    Tocher, D.A.3    Irving, E.4    Scheinmann, F.5
  • 107
    • 0032748434 scopus 로고    scopus 로고
    • Total synthesis of the antitumor marine sponge alkaloid agelastatin A
    • Stien, D.; Anderson, G.T.; Chase, C.E.; Koh, Y.-H.; Weinreb, S.M. Total synthesis of the antitumor marine sponge alkaloid agelastatin A. J. Am. Chem. Soc. 1999, 121, 9574-9579.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 9574-9579
    • Stien, D.1    Anderson, G.T.2    Chase, C.E.3    Koh, Y.-H.4    Weinreb, S.M.5
  • 108
    • 0037036711 scopus 로고    scopus 로고
    • Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B
    • Feldman, K.S.; Saunders, J.C. Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-agelastatin A and (-)-agelastatin B. J. Am. Chem. Soc. 2002, 124, 9060-9061.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 9060-9061
    • Feldman, K.S.1    Saunders, J.C.2
  • 109
    • 0037019981 scopus 로고    scopus 로고
    • Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B
    • Feldman, K.S.; Saunders, J.C.; Wrobleski, M.L. Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B. J. Org. Chem. 2002, 67, 7096-7109.
    • (2002) J. Org. Chem , vol.67 , pp. 7096-7109
    • Feldman, K.S.1    Saunders, J.C.2    Wrobleski, M.L.3
  • 110
    • 4043079398 scopus 로고    scopus 로고
    • New total synthesis of the marine antitumor alkaloid (-)-agelastatin A
    • Domostoj, M.M.; Irving, E.; Scheinmann, F.; Hale, K.J. New total synthesis of the marine antitumor alkaloid (-)-agelastatin A. Org. Lett. 2004, 6, 2615-2618.
    • (2004) Org. Lett , vol.6 , pp. 2615-2618
    • Domostoj, M.M.1    Irving, E.2    Scheinmann, F.3    Hale, K.J.4
  • 111
    • 14844365880 scopus 로고    scopus 로고
    • Asymmetric total synthesis of (-)-agelastatin A using sulfinimine (N-sulfinyl imine) derived methodologies
    • Davis, F.A.; Deng, J. Asymmetric total synthesis of (-)-agelastatin A using sulfinimine (N-sulfinyl imine) derived methodologies. Org. Lett. 2005, 7, 621-623.
    • (2005) Org. Lett , vol.7 , pp. 621-623
    • Davis, F.A.1    Deng, J.2
  • 112
    • 0002979399 scopus 로고    scopus 로고
    • The art and science of total synthesis at the dawn of the twenty-first century
    • Nicolaou, K.C.; Vourloumis, D.; Winssinger, N.; Baran, P.S. The art and science of total synthesis at the dawn of the twenty-first century. Angew. Chem., Int. Ed. 2000, 39, 44-122.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 44-122
    • Nicolaou, K.C.1    Vourloumis, D.2    Winssinger, N.3    Baran, P.S.4
  • 113
    • 0042379988 scopus 로고    scopus 로고
    • Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis
    • Trost, B.M.; Crawley, M.L. Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis. Chem. Rev. 2003, 103, 2921-2943.
    • (2003) Chem. Rev , vol.103 , pp. 2921-2943
    • Trost, B.M.1    Crawley, M.L.2
  • 114
    • 33646504646 scopus 로고    scopus 로고
    • New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A
    • Trost, B.M.; Dong, G. New class of nucleophiles for palladium-catalyzed asymmetric allylic alkylation. Total synthesis of agelastatin A. J. Am. Chem. Soc. 2006, 128, 6054-6055.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 6054-6055
    • Trost, B.M.1    Dong, G.2
  • 115
    • 67650502255 scopus 로고    scopus 로고
    • A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: Agelastatin A
    • Trost, B.M.; Dong, G. A stereodivergent strategy to both product enantiomers from the same enantiomer of a stereoinducing catalyst: Agelastatin A. Chem. Eur. J. 2009, 15, 6910-6919.
    • (2009) Chem. Eur. J , vol.15 , pp. 6910-6919
    • Trost, B.M.1    Dong, G.2
  • 116
    • 34547953030 scopus 로고    scopus 로고
    • Synthesis of (-)-agelastatin A by [3.3] sigmatropic rearrangement of allyl cyanate
    • Ichikawa, Y.; Yamaoka, T.; Nakano, K.; Kotsuki, H. Synthesis of (-)-agelastatin A by [3.3] sigmatropic rearrangement of allyl cyanate. Org. Lett. 2007, 9, 2989-2992.
    • (2007) Org. Lett , vol.9 , pp. 2989-2992
    • Ichikawa, Y.1    Yamaoka, T.2    Nakano, K.3    Kotsuki, H.4
  • 117
    • 61349122654 scopus 로고    scopus 로고
    • Total synthesis of (-)-agelastatin A
    • Yoshimitsu, T.; Ino, T.; Tanaka, T. Total synthesis of (-)-agelastatin A. Org. Lett. 2008, 10, 5457-5460.
    • (2008) Org. Lett , vol.10 , pp. 5457-5460
    • Yoshimitsu, T.1    Ino, T.2    Tanaka, T.3
  • 118
    • 68149141337 scopus 로고    scopus 로고
    • Total synthesis of the β-catenin inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination
    • Yoshimitsu, T.; Ino, T.; Futamura, N.; Kamon, T.; Tanaka, T. Total synthesis of the β-catenin inhibitor, (-)-agelastatin A: A second-generation approach based on radical aminobromination. Org. Lett. 2009, 11, 3402-3405.
    • (2009) Org. Lett , vol.11 , pp. 3402-3405
    • Yoshimitsu, T.1    Ino, T.2    Futamura, N.3    Kamon, T.4    Tanaka, T.5
  • 119
    • 70349786454 scopus 로고    scopus 로고
    • A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A
    • Wehn, P.M.; Du Bois, J. A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A. Angew. Chem., Int. Ed. 2009, 48, 3802-3805.
    • (2009) Angew. Chem., Int. Ed , vol.48 , pp. 3802-3805
    • Wehn, P.M.1    Du Bois, J.2
  • 120
    • 64049086842 scopus 로고    scopus 로고
    • Total synthesis of (±)-agelastatin A, a potent inhibitor of osteopontin-mediated neoplastic transformations
    • Dickson, D.P.; Wardrop, D.J. Total synthesis of (±)-agelastatin A, a potent inhibitor of osteopontin-mediated neoplastic transformations. Org. Lett. 2009, 11, 1341-1344.
    • (2009) Org. Lett , vol.11 , pp. 1341-1344
    • Dickson, D.P.1    Wardrop, D.J.2
  • 121
    • 67149128368 scopus 로고    scopus 로고
    • Total synthesis of (-)-agelastatin A: The application of a sequential sigmatropic rearrangement
    • Hama, N.; Matsuda, T.; Sato, T.; Chida, N. Total synthesis of (-)-agelastatin A: The application of a sequential sigmatropic rearrangement. Org. Lett. 2009, 11, 2687-2690.
    • (2009) Org. Lett , vol.11 , pp. 2687-2690
    • Hama, N.1    Matsuda, T.2    Sato, T.3    Chida, N.4
  • 123
    • 64349112135 scopus 로고    scopus 로고
    • Total synthesis of the putative structure of nagelamide D
    • Bhandari, M.R.; Sivappa, R.; Lovely, C.J. Total synthesis of the putative structure of nagelamide D. Org. Lett. 2009, 11, 1535-1538.
    • (2009) Org. Lett , vol.11 , pp. 1535-1538
    • Bhandari, M.R.1    Sivappa, R.2    Lovely, C.J.3
  • 125
    • 19844364290 scopus 로고    scopus 로고
    • Significant enhancement of the Stille reaction with a new combination of reagents-copper(I) iodide with cesium fluoride
    • Mee, S.P.H.; Lee, V.; Baldwin, J.E. Significant enhancement of the Stille reaction with a new combination of reagents-copper(I) iodide with cesium fluoride. Chem. Eur. J. 2005, 11, 3294-3308.
    • (2005) Chem. Eur. J , vol.11 , pp. 3294-3308
    • Mee, S.P.H.1    Lee, V.2    Baldwin, J.E.3
  • 126
    • 70349488843 scopus 로고    scopus 로고
    • Recent synthetic studies leading to structural revisions of marine natural products
    • Usami, Y. Recent synthetic studies leading to structural revisions of marine natural products. Mar. Drugs 2009, 7, 314-330.
    • (2009) Mar. Drugs , vol.7 , pp. 314-330
    • Usami, Y.1
  • 127
    • 0019825508 scopus 로고
    • Sceptrin, an antimicrobial agent from the sponge Agelas sceptrum
    • Walker, R.P.; Faulkner, D.J.; Van Engen, D.; Clardy, J. Sceptrin, an antimicrobial agent from the sponge Agelas sceptrum. J. Am. Chem. Soc. 1981, 103, 6772-6773.
    • (1981) J. Am. Chem. Soc , vol.103 , pp. 6772-6773
    • Walker, R.P.1    Faulkner, D.J.2    Van Engen, D.3    Clardy, J.4
  • 128
    • 0032583698 scopus 로고    scopus 로고
    • Photochemical dimerization of esters of urocanic acid
    • D'Auria, M.; Racioppi, R. Photochemical dimerization of esters of urocanic acid. J. Photochem. Photobiol. 1998, 112, 145-148.
    • (1998) J. Photochem. Photobiol , vol.112 , pp. 145-148
    • D'Auria, M.1    Racioppi, R.2
  • 130
    • 3242696362 scopus 로고    scopus 로고
    • Synthesis of sceptrin alkaloids
    • Birman, V.B.; Jiang, X.-T. Synthesis of sceptrin alkaloids. Org. Lett. 2004, 6, 2369-2371.
    • (2004) Org. Lett , vol.6 , pp. 2369-2371
    • Birman, V.B.1    Jiang, X.-T.2
  • 131
    • 29544436227 scopus 로고    scopus 로고
    • Short, enantioselective total synthesis of sceptrin and ageliferin by programmed oxaquadricyclane fragmentation
    • Baran, P.S.; Li, K.; O'Malley, D.P.; Mitsos, C. Short, enantioselective total synthesis of sceptrin and ageliferin by programmed oxaquadricyclane fragmentation. Angew. Chem., Int. Ed. 2006, 45, 249-252.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 249-252
    • Baran, P.S.1    Li, K.2    O'Malley, D.P.3    Mitsos, C.4
  • 132
    • 34247515502 scopus 로고    scopus 로고
    • Total synthesis of dimeric pyrrole-imidazole alkaloids: Sceptrin, ageliferin, nagelamide E, oxysceptrin, nakamuric acid, and the axinellamine carbon skeleton
    • O'Malley, D.P.; Li, K.; Maue, M.; Zografos, A.L.; Baran, P.S. Total synthesis of dimeric pyrrole-imidazole alkaloids: Sceptrin, ageliferin, nagelamide E, oxysceptrin, nakamuric acid, and the axinellamine carbon skeleton. J. Am. Chem. Soc. 2007, 129, 4762-4775.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 4762-4775
    • O'Malley, D.P.1    Li, K.2    Maue, M.3    Zografos, A.L.4    Baran, P.S.5
  • 133
    • 1642319938 scopus 로고
    • Nucleophilic cleavage of quadricyclene-2,3-dicarboxylate derivatives by iodide
    • Nelsen, S.F.; Calabrese, J.C. Nucleophilic cleavage of quadricyclene-2,3-dicarboxylate derivatives by iodide. J. Am. Chem. Soc. 1973, 95, 8385-8389.
    • (1973) J. Am. Chem. Soc , vol.95 , pp. 8385-8389
    • Nelsen, S.F.1    Calabrese, J.C.2
  • 134
    • 84984281414 scopus 로고
    • Halogenation using quaternary ammonium polyhalides. Part X. α-Chlorination of aromatic acetyl derivatives with benzyltrimethylammonium dichloroiodate
    • Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Fujisaki, S.; Maeno, K.; Okamoto, T. Halogenation using quaternary ammonium polyhalides. Part X. α-Chlorination of aromatic acetyl derivatives with benzyltrimethylammonium dichloroiodate. Synthesis 1988, 545-546.
    • (1988) Synthesis , pp. 545-546
    • Kajigaeshi, S.1    Kakinami, T.2    Moriwaki, M.3    Fujisaki, S.4    Maeno, K.5    Okamoto, T.6
  • 135
    • 0014578449 scopus 로고
    • Synthesis and relationship between structure and activity of 2-nitroimidazole derivatives
    • Lancini, G.C.; Lazzari, E.; Arioli, V.; Bellani, P. Synthesis and relationship between structure and activity of 2-nitroimidazole derivatives. J. Med. Chem. 1969, 12, 775-780.
    • (1969) J. Med. Chem , vol.12 , pp. 775-780
    • Lancini, G.C.1    Lazzari, E.2    Arioli, V.3    Bellani, P.4
  • 138
    • 0031733121 scopus 로고    scopus 로고
    • Debromosceptrin, an alkaloid from the Caribbean sponge Agelas conifera
    • Shen, X.; Perry, T.L.; Dunbar, C.D.; Kelly-Borges, M.; Hamann, M.T. Debromosceptrin, an alkaloid from the Caribbean sponge Agelas conifera. J. Nat. Prod. 1998, 61, 1302-1303.
    • (1998) J. Nat. Prod , vol.61 , pp. 1302-1303
    • Shen, X.1    Perry, T.L.2    Dunbar, C.D.3    Kelly-Borges, M.4    Hamann, M.T.5
  • 140
    • 0030022491 scopus 로고    scopus 로고
    • Naturally occurring somatostatin and vasoactive intestinal peptide inhibitors. Isolation of alkaloids from two marine sponges
    • Vassas, A.; Bourdy, G.; Paillard, J.J.; Lavayre, J.; Pais, M.; Quirion, J.C.; Debitus, C. Naturally occurring somatostatin and vasoactive intestinal peptide inhibitors. Isolation of alkaloids from two marine sponges. Planta Med. 1996, 62, 28-30.
    • (1996) Planta Med , vol.62 , pp. 28-30
    • Vassas, A.1    Bourdy, G.2    Paillard, J.J.3    Lavayre, J.4    Pais, M.5    Quirion, J.C.6    Debitus, C.7
  • 141
    • 44949095586 scopus 로고    scopus 로고
    • Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol
    • Rodriguez, A.D.; Lear, M.J.; La Clair, J.J. Identification of the binding of sceptrin to MreB via a bidirectional affinity protocol. J. Am. Chem. Soc. 2008, 130, 7256-7258.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 7256-7258
    • Rodriguez, A.D.1    Lear, M.J.2    La Clair, J.J.3
  • 142
    • 13544274210 scopus 로고    scopus 로고
    • MreB actin-mediated segregation of a specific region of a bacterial chromosome
    • Gitai, Z.; Dye, N.A.; Reisenauer, A.; Wachi, M.; Shapiro, L. MreB actin-mediated segregation of a specific region of a bacterial chromosome. Cell 2005, 120, 329-341.
    • (2005) Cell , vol.120 , pp. 329-341
    • Gitai, Z.1    Dye, N.A.2    Reisenauer, A.3    Wachi, M.4    Shapiro, L.5
  • 143
    • 0001759287 scopus 로고
    • Biologically active marine natural products
    • Rinehart, K.L. Biologically active marine natural products. Pure Appl. Chem. 1989, 61, 525-528.
    • (1989) Pure Appl. Chem , vol.61 , pp. 525-528
    • Rinehart, K.L.1
  • 145
    • 0036128521 scopus 로고    scopus 로고
    • Bromosceptrin, an alkaloid from the marine sponge Agelas conifera
    • Assmann, M.; Köck, M. Bromosceptrin, an alkaloid from the marine sponge Agelas conifera. Z. Naturforsch., C J. Biosci. 2002, 57, 157-160.
    • (2002) Z. Naturforsch., C J. Biosci , vol.57 , pp. 157-160
    • Assmann, M.1    Köck, M.2
  • 146
    • 33746321900 scopus 로고    scopus 로고
    • Mechanism of the vinylcyclobutane rearrangement of sceptrin to ageliferin and nagelamide E
    • Northrop, B.H.; O'Malley, D.P.; Zografos, A.L.; Baran, P.S.; Houk, K.N. Mechanism of the vinylcyclobutane rearrangement of sceptrin to ageliferin and nagelamide E. Angew. Chem., Int. Ed. 2006, 45, 4126-4130.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 4126-4130
    • Northrop, B.H.1    O'Malley, D.P.2    Zografos, A.L.3    Baran, P.S.4    Houk, K.N.5
  • 147
    • 33746288746 scopus 로고    scopus 로고
    • III-mediated oxidative heterobicyclizations: Access to the core skeletons of oroidin dimers
    • III-mediated oxidative heterobicyclizations: Access to the core skeletons of oroidin dimers. Angew. Chem., Int. Ed. 2006, 45, 4345-4348.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 4345-4348
    • Tan, X.1    Chen, C.2
  • 149
    • 0027212254 scopus 로고
    • A cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata
    • Kinnel, R.B.; Gehrken, H.P.; Scheuer, P.J. Palau'amine: A cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata. J. Am. Chem. Soc. 1993, 115, 3376-3377.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 3376-3377
    • Kinnel, R.B.1    Gehrken, H.P.2    Scheuer3    Palau'amine, P.J.4
  • 151
    • 34247481744 scopus 로고    scopus 로고
    • Structural assignment of tetrabromostyloguanidine: Does the relative configuration of the palau'amines need revision?
    • Grube, A.; Köck, M. Structural assignment of tetrabromostyloguanidine: Does the relative configuration of the palau'amines need revision? Angew. Chem., Int. Ed. 2007, 46, 2320-2324.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 2320-2324
    • Grube, A.1    Köck, M.2
  • 154
    • 57549105232 scopus 로고    scopus 로고
    • Total syntheses of (±)-massadine and massadine chloride
    • Su, S.; Seiple, I.B.; Young, I.S.; Baran, P.S. Total syntheses of (±)-massadine and massadine chloride. J. Am. Chem. Soc. 2008, 130, 16490-16491.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 16490-16491
    • Su, S.1    Seiple, I.B.2    Young, I.S.3    Baran, P.S.4
  • 155
    • 1642414157 scopus 로고    scopus 로고
    • Oxidative rearrangement of imidazoles with dimethyldioxirane
    • Lovely, C.J.; Du, H.; He, Y.; Dias, H.V.R. Oxidative rearrangement of imidazoles with dimethyldioxirane. Org. Lett. 2004, 6, 735-738.
    • (2004) Org. Lett , vol.6 , pp. 735-738
    • Lovely, C.J.1    Du, H.2    He, Y.3    Dias, H.V.R.4
  • 156
    • 0035902247 scopus 로고    scopus 로고
    • Enantioselective strategy to the spirocyclic core of palau'amine and related bisguanidine marine alkaloids
    • Dilley, A.S.; Romo, D. Enantioselective strategy to the spirocyclic core of palau'amine and related bisguanidine marine alkaloids. Org. Lett. 2001, 3, 1535-1538.
    • (2001) Org. Lett , vol.3 , pp. 1535-1538
    • Dilley, A.S.1    Romo, D.2
  • 157
    • 33744984312 scopus 로고    scopus 로고
    • A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
    • Dransfield, P.J.; Dilley, A.S.; Wang, S.; Romo, D. A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal. Tetrahedron 2006, 62, 5223-5247.
    • (2006) Tetrahedron , vol.62 , pp. 5223-5247
    • Dransfield, P.J.1    Dilley, A.S.2    Wang, S.3    Romo, D.4
  • 158
    • 55949084048 scopus 로고    scopus 로고
    • Zancanella, M.A.; Romo, D. Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate. Org. Lett. 2008, 10, 3685-3688.
    • Zancanella, M.A.; Romo, D. Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate. Org. Lett. 2008, 10, 3685-3688.
  • 159
    • 41249086158 scopus 로고    scopus 로고
    • Enantioselective synthesis of (+)-monobromophakellin and (+)-phakellin: A concise phakellin annulation strategy applicable to palau'amine
    • Wang, S.; Romo, D. Enantioselective synthesis of (+)-monobromophakellin and (+)-phakellin: A concise phakellin annulation strategy applicable to palau'amine. Angew. Chem., Int. Ed. 2008, 47, 1284-1286.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 1284-1286
    • Wang, S.1    Romo, D.2
  • 160
    • 4544360320 scopus 로고    scopus 로고
    • Studies towards the total synthesis of palau'amine. Formation of 4,5-dihydropyrrole-2-carboxylate intermediates by alkene-enamide ring-closing metathesis
    • Katz, J.D.; Overman, L.E. Studies towards the total synthesis of palau'amine. Formation of 4,5-dihydropyrrole-2-carboxylate intermediates by alkene-enamide ring-closing metathesis. Tetrahedron 2004, 60, 9559-9568.
    • (2004) Tetrahedron , vol.60 , pp. 9559-9568
    • Katz, J.D.1    Overman, L.E.2
  • 161
    • 35548960983 scopus 로고    scopus 로고
    • On the structure of palau'amine: Evidence for the revised relative configuration from chemical synthesis
    • Lanman, B.A.; Overman, L.E.; Paulini, R.; White, N.S. On the structure of palau'amine: Evidence for the revised relative configuration from chemical synthesis. J. Am. Chem. Soc. 2007, 129, 12896-12900.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 12896-12900
    • Lanman, B.A.1    Overman, L.E.2    Paulini, R.3    White, N.S.4
  • 163
    • 0033524887 scopus 로고    scopus 로고
    • Axinellamines A-D, novel imidazo-azolo-imidazole alkaloids from the Australian marine sponge Axinella sp
    • Urban, S.; Leone, P.D.A.; Carroll, A.R.; Fechner, G.A.; Smith, J.; Hooper, J.N.A.; Quinn, R.J. Axinellamines A-D, novel imidazo-azolo-imidazole alkaloids from the Australian marine sponge Axinella sp. J. Org. Chem. 1999, 64, 731-735.
    • (1999) J. Org. Chem , vol.64 , pp. 731-735
    • Urban, S.1    Leone, P.D.A.2    Carroll, A.R.3    Fechner, G.A.4    Smith, J.5    Hooper, J.N.A.6    Quinn, R.J.7
  • 164
    • 48849102896 scopus 로고    scopus 로고
    • Synthesis of marine alkaloids from the oroidin family
    • Arndt, H.-D.; Riedrich, M. Synthesis of marine alkaloids from the oroidin family. Angew. Chem., Int. Ed. 2008, 47, 4785-4788.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 4785-4788
    • Arndt, H.-D.1    Riedrich, M.2
  • 165
    • 0034644391 scopus 로고    scopus 로고
    • Enantioselective synthesis of the cyclopentyl core of the axinellamines
    • Starr, J.T.; Koch, G.; Carreira, E.M. Enantioselective synthesis of the cyclopentyl core of the axinellamines. J. Am. Chem. Soc. 2000, 122, 8793-8794.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 8793-8794
    • Starr, J.T.1    Koch, G.2    Carreira, E.M.3
  • 166
    • 18844385988 scopus 로고    scopus 로고
    • Highly regioselective Diels-Alder reactions toward oroidin alkaloids: Use of a tosylvinyl moiety as a nitrogen masking group with adjustable electronics
    • Dransfield, P.J.; Wang, S.; Dilley, A.; Romo, D. Highly regioselective Diels-Alder reactions toward oroidin alkaloids: Use of a tosylvinyl moiety as a nitrogen masking group with adjustable electronics. Org. Lett. 2005, 7, 1679-1682.
    • (2005) Org. Lett , vol.7 , pp. 1679-1682
    • Dransfield, P.J.1    Wang, S.2    Dilley, A.3    Romo, D.4
  • 167
    • 0028936559 scopus 로고
    • Styloguanidines, new chitinase inhibitors from the marine sponge Stylotella aurantium
    • Kato, T.; Shizuri, Y.; Izumida, H.; Yokoyama, A.; Endo, M. Styloguanidines, new chitinase inhibitors from the marine sponge Stylotella aurantium. Tetrahedron Lett. 1995, 36, 2133-2136.
    • (1995) Tetrahedron Lett , vol.36 , pp. 2133-2136
    • Kato, T.1    Shizuri, Y.2    Izumida, H.3    Yokoyama, A.4    Endo, M.5
  • 168
    • 0037500376 scopus 로고    scopus 로고
    • Enantioselective total synthesis of (+)-dibromophakellstatin
    • Poullennec, K.G.; Romo, D. Enantioselective total synthesis of (+)-dibromophakellstatin. J. Am. Chem. Soc. 2003, 125, 6344-6345.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 6344-6345
    • Poullennec, K.G.1    Romo, D.2
  • 169
    • 33646541402 scopus 로고    scopus 로고
    • New methods of imidazole functionalization - from imidazole to marine alkaloids
    • Du, H.; He, Y.; Rasapalli, S.; Lovely, C.J. New methods of imidazole functionalization - from imidazole to marine alkaloids. Synlett 2006, 965-992.
    • (2006) Synlett , pp. 965-992
    • Du, H.1    He, Y.2    Rasapalli, S.3    Lovely, C.J.4
  • 170
    • 35048820403 scopus 로고    scopus 로고
    • Studies toward the total synthesis of axinellamine and massadine
    • Sivappa, R.; Hernandez, N.M.; He, Y.; Lovely, C.J. Studies toward the total synthesis of axinellamine and massadine. Org. Lett. 2007, 9, 3861-3864.
    • (2007) Org. Lett , vol.9 , pp. 3861-3864
    • Sivappa, R.1    Hernandez, N.M.2    He, Y.3    Lovely, C.J.4
  • 172
    • 0036827533 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of triazacyclopenta[cd] pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines
    • Belanger, G.; Hong, F.-T.; Overman, L.E.; Rogers, B.N.; Tellew, J.E.; Trenkle, W.C. Stereocontrolled synthesis of triazacyclopenta[cd] pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines. J. Org. Chem. 2002, 67, 7880-7883.
    • (2002) J. Org. Chem , vol.67 , pp. 7880-7883
    • Belanger, G.1    Hong, F.-T.2    Overman, L.E.3    Rogers, B.N.4    Tellew, J.E.5    Trenkle, W.C.6
  • 173
    • 34047170718 scopus 로고    scopus 로고
    • Evaluation of strategies for the synthesis of the guanidine hemiaminal portion of palau'amine
    • Lanman, B.A.; Overman, L.E. Evaluation of strategies for the synthesis of the guanidine hemiaminal portion of palau'amine. Heterocycles 2006, 70, 557-570.
    • (2006) Heterocycles , vol.70 , pp. 557-570
    • Lanman, B.A.1    Overman, L.E.2
  • 174
    • 0141518620 scopus 로고    scopus 로고
    • A Transient N-O-linked Pauson-Khand strategy for the synthesis of the deschloro carbocyclic core of the palau'amines and styloguanidines
    • König, S.G.; Miller, S.M.; Leonard, K.A.; Loewe, R.S.; Chen, B.C.; Austin, D.J. A Transient N-O-linked Pauson-Khand strategy for the synthesis of the deschloro carbocyclic core of the palau'amines and styloguanidines. Org. Lett. 2003, 5, 2203-2206.
    • (2003) Org. Lett , vol.5 , pp. 2203-2206
    • König, S.G.1    Miller, S.M.2    Leonard, K.A.3    Loewe, R.S.4    Chen, B.C.5    Austin, D.J.6
  • 175
    • 33750366010 scopus 로고    scopus 로고
    • Stylissadines A and B: The first tetrameric pyrrole-imidazole alkaloids
    • Grube, A.; Köck, M. Stylissadines A and B: The first tetrameric pyrrole-imidazole alkaloids. Org. Lett. 2006, 8, 4675-4678.
    • (2006) Org. Lett , vol.8 , pp. 4675-4678
    • Grube, A.1    Köck, M.2
  • 176
    • 34047195642 scopus 로고    scopus 로고
    • Natural products, stylissadines A and B, specific antagonists of the P2X7 receptor, an important inflammatory target
    • Buchanan, M.S.; Carroll, A.R.; Addepalli, R.; Avery, V.M.; Hooper, J.N.A.; Quinn, R.J. Natural products, stylissadines A and B, specific antagonists of the P2X7 receptor, an important inflammatory target. J. Org. Chem. 2007, 72, 2309-2317.
    • (2007) J. Org. Chem , vol.72 , pp. 2309-2317
    • Buchanan, M.S.1    Carroll, A.R.2    Addepalli, R.3    Avery, V.M.4    Hooper, J.N.A.5    Quinn, R.J.6
  • 177
    • 0345733986 scopus 로고    scopus 로고
    • Fujita, M.; Nakao, Y.; Matsunaga, S.; Seiki, M.; Itoh, Y.; Yamashita, J.; Van Soest, R.W.M.; Fusetani, N. Ageladine A: An antiangiogenic matrix metalloproteinase inhibitor from the marine sponge Agelas nakamurai. J. Am. Chem. Soc. 2003, 125, 15700-15701.
    • Fujita, M.; Nakao, Y.; Matsunaga, S.; Seiki, M.; Itoh, Y.; Yamashita, J.; Van Soest, R.W.M.; Fusetani, N. Ageladine A: An antiangiogenic matrix metalloproteinase inhibitor from the marine sponge Agelas nakamurai. J. Am. Chem. Soc. 2003, 125, 15700-15701.
  • 178
    • 33645919009 scopus 로고    scopus 로고
    • Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai
    • Meketa, M.L.; Weinreb, S.M. Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai. Org. Lett. 2006, 8, 1443-1446.
    • (2006) Org. Lett , vol.8 , pp. 1443-1446
    • Meketa, M.L.1    Weinreb, S.M.2
  • 179
    • 34250898546 scopus 로고    scopus 로고
    • Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues
    • Meketa, M.L.; Weinreb, S.M.; Nakao, Y.; Fusetani, N. Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues. J. Org. Chem. 2007, 72, 4892-4899.
    • (2007) J. Org. Chem , vol.72 , pp. 4892-4899
    • Meketa, M.L.1    Weinreb, S.M.2    Nakao, Y.3    Fusetani, N.4
  • 180
    • 33947154321 scopus 로고    scopus 로고
    • A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine A featuring a biogenetically patterned 6π-2-azatriene electrocyclization
    • Meketa, M.L.; Weinreb, S.M. A new total synthesis of the zinc matrixmetalloproteinase inhibitor ageladine A featuring a biogenetically patterned 6π-2-azatriene electrocyclization. Org. Lett. 2007, 9, 853-855.
    • (2007) Org. Lett , vol.9 , pp. 853-855
    • Meketa, M.L.1    Weinreb, S.M.2
  • 181
    • 34547465242 scopus 로고    scopus 로고
    • A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization
    • Meketa, M.L.; Weinreb, S.M. A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization. Tetrahedron 2007, 63, 9112-9119.
    • (2007) Tetrahedron , vol.63 , pp. 9112-9119
    • Meketa, M.L.1    Weinreb, S.M.2
  • 182
    • 33748944826 scopus 로고    scopus 로고
    • Concise total synthesis of the marine natural product ageladine A
    • Shengule, S.R.; Karuso, P. Concise total synthesis of the marine natural product ageladine A. Org. Lett. 2006, 8, 4083-4084.
    • (2006) Org. Lett , vol.8 , pp. 4083-4084
    • Shengule, S.R.1    Karuso, P.2
  • 183
    • 34447328084 scopus 로고    scopus 로고
    • Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs
    • Ando, N.; Terashima, S. Synthesis and matrix metalloproteinase (MMP)-12 inhibitory activity of ageladine A and its analogs. Bioorg. Med. Chem. Lett. 2007, 17, 4495-4499.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 4495-4499
    • Ando, N.1    Terashima, S.2
  • 184
    • 47249102446 scopus 로고    scopus 로고
    • Bickmeyer, U.; Grube, A.; Klings, K.-W.; Köck, M. Ageladine A, a pyrrole-imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye. Biochem. Biophys. Res. Commun. 2008, 373, 419-422.
    • Bickmeyer, U.; Grube, A.; Klings, K.-W.; Köck, M. Ageladine A, a pyrrole-imidazole alkaloid from marine sponges, is a pH sensitive membrane permeable dye. Biochem. Biophys. Res. Commun. 2008, 373, 419-422.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.