메뉴 건너뛰기




Volumn 8, Issue 8, 2010, Pages 2395-2416

New one-pot methodologies for the modification or synthesis of alkaloid scaffolds

Author keywords

Cascade reactions; Marine alkaloids; One pot synthesis; Organocatalysis; Semisynthesis; Total synthesis

Indexed keywords

6 CYCLOHEXAMIDOMANZAMINE A; 8 HYDROXYMANZAMINE A; ALKALOID; AMINOMANZAMINE DERIVATIVE; AROMATIC NITRO COMPOUND; BETA CARBOLINE DERIVATIVE; BETA LACTAM DERIVATIVE; BISTELLETTAZOLE A; HEXAHYDROPYRROLIZINE DERIVATIVE; INDOLOQUINOLIZIDINE DERIVATIVE; IRCINAL A; LEPADIFORMINE; MANZAMINE A; NATURAL PRODUCT; OCTAHYDROINDOLIZINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; SCHULZENINE A; SCHULZENINE B; SCHULZENINE C; UNCLASSIFIED DRUG;

EID: 77956416781     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md8082395     Document Type: Review
Times cited : (23)

References (38)
  • 1
    • 84889430517 scopus 로고    scopus 로고
    • Manzamine alkaloids
    • Fattorusso, E., Taglialatela-Scafati, O., Eds.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany
    • Peng, J.; Rao, K.V.; Choo, Y.M.; Hamann, M.T. Manzamine alkaloids. In Modern Alkaloids; Fattorusso, E., Taglialatela-Scafati, O., Eds.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2007; pp. 189-232.
    • (2007) Modern Alkaloids , pp. 189-232
    • Peng, J.1    Rao, K.V.2    Choo, Y.M.3    Hamann, M.T.4
  • 2
    • 7044235263 scopus 로고    scopus 로고
    • Domino reactions in organic synthesis
    • Tietze, L.F. Domino reactions in organic synthesis. Chem. Rev. 1996, 96, 115-136.
    • (1996) Chem. Rev. , vol.96 , pp. 115-136
    • Tietze, L.F.1
  • 3
    • 33750173220 scopus 로고
    • Sequential transformations in organic chemistry: A synthetic strategy with a future
    • Tietze, L.F.; Beifuss, U. Sequential transformations in organic chemistry: A synthetic strategy with a future. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
    • (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 131-163
    • Tietze, L.F.1    Beifuss, U.2
  • 4
    • 0037423972 scopus 로고    scopus 로고
    • Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis
    • Nicolaou, K.C.; Montagnon, T.; Snyder, S.A. Tandem reactions, cascade sequences, and biomimetic strategies in total synthesis. Chem. Commun. 2003, 5, 551-564.
    • (2003) Chem. Commun. , vol.5 , pp. 551-564
    • Nicolaou, K.C.1    Montagnon, T.2    Snyder, S.A.3
  • 6
    • 70350519146 scopus 로고    scopus 로고
    • The art of total synthesis through cascade reactions
    • Nicolaou, K.C.; Chen, S.J. The art of total synthesis through cascade reactions. Chem. Soc. Rev. 2009, 38, 2993-3009.
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 2993-3009
    • Nicolaou, K.C.1    Chen, S.J.2
  • 7
    • 31544452548 scopus 로고    scopus 로고
    • Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries
    • Pellissier, H. Asymmetric domino reactions. Part A: reactions based on the use of chiral auxiliaries. Tetrahedron 2006, 62, 1619-1665.
    • (2006) Tetrahedron , vol.62 , pp. 1619-1665
    • Pellissier, H.1
  • 8
    • 32544440478 scopus 로고    scopus 로고
    • Asymmetric domino reactions. Part B: Reactions based on the use of chiral catalysts and biocatalysts
    • Pellissier, H. Asymmetric domino reactions. Part B: reactions based on the use of chiral catalysts and biocatalysts. Tetrahedron 2006, 62, 2143-2173.
    • (2006) Tetrahedron , vol.62 , pp. 2143-2173
    • Pellissier, H.1
  • 9
    • 70350511179 scopus 로고    scopus 로고
    • Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis
    • Padwa, A. Domino reactions of rhodium(ii) carbenoids for alkaloid synthesis. Chem. Soc. Rev. 2009, 38, 3072-3081.
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 3072-3081
    • Padwa, A.1
  • 10
    • 34250021382 scopus 로고    scopus 로고
    • The domino way to heterocycles
    • Padwa, A.; Bur, S.K. The domino way to heterocycles. Tetrahedron 2007, 63, 5341-5378.
    • (2007) Tetrahedron , vol.63 , pp. 5341-5378
    • Padwa, A.1    Bur, S.K.2
  • 11
    • 27744521817 scopus 로고    scopus 로고
    • Development of new synthetic methods and its applications to total synthesis of nitrogen-containing bioactive natural products
    • Kibayashi, C. Development of new synthetic methods and its applications to total synthesis of nitrogen-containing bioactive natural products. Chem. Pharm. Bull. 2005, 53, 1375-1386.
    • (2005) Chem. Pharm. Bull. , vol.53 , pp. 1375-1386
    • Kibayashi, C.1
  • 13
    • 4344668984 scopus 로고    scopus 로고
    • Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases
    • Rao, K.V.; Kasanah, N.; Wahyuono, S.; Tekwani, B.L.; Schinazi, R.F.; Hamann, M.T. Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases. J. Nat. Prod. 2004, 67, 1314-1318.
    • (2004) J. Nat. Prod. , vol.67 , pp. 1314-1318
    • Rao, K.V.1    Kasanah, N.2    Wahyuono, S.3    Tekwani, B.L.4    Schinazi, R.F.5    Hamann, M.T.6
  • 15
    • 71749102449 scopus 로고    scopus 로고
    • Structure activity relationship studies of manzamine A: Amidation of positions 6 and 8 of the β-carboline moiety
    • Wahba, A.E.; Peng, J.; Kudrimoti, S.; Tekwani, B.L.; Hamann, M.T. Structure activity relationship studies of manzamine A: amidation of positions 6 and 8 of the β-carboline moiety. Bioorg. Med. Chem. 2009, 17, 7775-7782.
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 7775-7782
    • Wahba, A.E.1    Peng, J.2    Kudrimoti, S.3    Tekwani, B.L.4    Hamann, M.T.5
  • 16
    • 49049086287 scopus 로고    scopus 로고
    • Kinetic studies and bioactivity of potential manzamine prodrugs
    • Shilabin, A.G.; Kasanah, N.; Tekwani, B.L.; Hamann, M.T. Kinetic studies and bioactivity of potential manzamine prodrugs. J. Nat. Prod. 2008, 71, 1218-1221.
    • (2008) J. Nat. Prod. , vol.71 , pp. 1218-1221
    • Shilabin, A.G.1    Kasanah, N.2    Tekwani, B.L.3    Hamann, M.T.4
  • 19
    • 65549124005 scopus 로고    scopus 로고
    • Reductive amidation of nitroarenes: A practical approach for the amidation of natural products
    • Wahba, A.E.; Peng, J.; Hamann, M.T. Reductive amidation of nitroarenes: a practical approach for the amidation of natural products. Tetrahedron Lett. 2009, 50, 3901-3904.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 3901-3904
    • Wahba, A.E.1    Peng, J.2    Hamann, M.T.3
  • 21
    • 7044229545 scopus 로고    scopus 로고
    • Tetradehydrohalicyclamine A and 22-hydroxyhalicyclamine A, new cytotoxic bis-piperidine alkaloids from a marine sponge amphimedon sp
    • Matsunaga, S.; Miyata, Y.; van Soest, R.W.M.; Fusetani, N. Tetradehydrohalicyclamine A and 22-hydroxyhalicyclamine A, new cytotoxic bis-piperidine alkaloids from a marine sponge amphimedon sp. J. Nat. Prod. 2004, 67, 1758-1760.
    • (2004) J. Nat. Prod. , vol.67 , pp. 1758-1760
    • Matsunaga, S.1    Miyata, Y.2    Van Soest, R.W.M.3    Fusetani, N.4
  • 22
    • 65649088354 scopus 로고    scopus 로고
    • Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp
    • Ishiguro, Y.; Kubota, T.; Ishiuchi, K.; Fromont, J.; Kobayashi, J. Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp. Tetrahedron Lett. 2009, 50, 3202-3204.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 3202-3204
    • Ishiguro, Y.1    Kubota, T.2    Ishiuchi, K.3    Fromont, J.4    Kobayashi, J.5
  • 23
    • 33751025895 scopus 로고    scopus 로고
    • Chiral Oxazolopiperidone Lactams: Versatile Intermediates for the Enantioselective Synthesis of Piperidine-Containing Natural Products
    • Escolano, C.; Amat, M.; Bosch, J. Chiral Oxazolopiperidone Lactams: Versatile Intermediates for the Enantioselective Synthesis of Piperidine-Containing Natural Products. Chem. Eur. J. 2006, 12, 8198-8207.
    • (2006) Chem. Eur. J. , vol.12 , pp. 8198-8207
    • Escolano, C.1    Amat, M.2    Bosch, J.3
  • 24
    • 0141925985 scopus 로고    scopus 로고
    • Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring-closing metathesis as a key step
    • Felpin, F.; Lebreton, J. Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring-closing metathesis as a key step. Eur. J. Org. Chem. 2003, 2003, 3693-3712.
    • (2003) Eur. J. Org. Chem. , vol.2003 , pp. 3693-3712
    • Felpin, F.1    Lebreton, J.2
  • 25
    • 0033709712 scopus 로고    scopus 로고
    • Stereoselective synthesis of piperidines
    • Laschat, S.; Dickner, T. Stereoselective synthesis of piperidines. Synthesis 2000, 2000, 1781-1813.
    • (2000) Synthesis , vol.2000 , pp. 1781-1813
    • Laschat, S.1    Dickner, T.2
  • 26
    • 35948958951 scopus 로고    scopus 로고
    • Intermolecular cross-double-Michael addition between nitro and carbonyl activated olefins as a new approach in C-C bond formation
    • Sun, X.; Sengupta, S.; Petersen, J.L.; Wang, H.; Lewis, J.P.; Shi, X. Intermolecular cross-double-Michael addition between nitro and carbonyl activated olefins as a new approach in C-C bond formation. Org. Lett. 2007, 9, 4495-4498.
    • (2007) Org. Lett. , vol.9 , pp. 4495-4498
    • Sun, X.1    Sengupta, S.2    Petersen, J.L.3    Wang, H.4    Lewis, J.P.5    Shi, X.6
  • 27
    • 66149176807 scopus 로고    scopus 로고
    • One-pot asymmetric synthesis of substituted piperidines by exocyclic chirality induction
    • Chen, Y.; Zhong, C.; Petersen, J.L.; Akhmedov, N.G.; Shi, X. One-pot asymmetric synthesis of substituted piperidines by exocyclic chirality induction. Org. Lett. 2009, 11, 2333-2336.
    • (2009) Org. Lett. , vol.11 , pp. 2333-2336
    • Chen, Y.1    Zhong, C.2    Petersen, J.L.3    Akhmedov, N.G.4    Shi, X.5
  • 28
    • 58249101213 scopus 로고    scopus 로고
    • Asymmetric alkaloid synthesis: A one-pot organocatalytic reaction to quinolizidine derivatives
    • Franzen, J.; Fisher, A. Asymmetric alkaloid synthesis: a one-pot organocatalytic reaction to quinolizidine derivatives. Angew. Chem. Int. Ed. Engl. 2009, 48, 787-791.
    • (2009) Angew. Chem. Int. Ed. Engl. , vol.48 , pp. 787-791
    • Franzen, J.1    Fisher, A.2
  • 31
    • 66149124126 scopus 로고    scopus 로고
    • Organocatalytic approach to enantioselective one-pot synthesis of pyrrolidine, hexahydropyrrolizine, and octahydroindolizine core structures
    • Wang, Y.; Kumano, T.; Kano, T.; Maruoka, K. Organocatalytic approach to enantioselective one-pot synthesis of pyrrolidine, hexahydropyrrolizine, and octahydroindolizine core structures. Org. Lett. 2009, 11, 2027-2029.
    • (2009) Org. Lett. , vol.11 , pp. 2027-2029
    • Wang, Y.1    Kumano, T.2    Kano, T.3    Maruoka, K.4
  • 32
    • 55449131371 scopus 로고    scopus 로고
    • Bistellettazines A-C and Bistellettazole A: New Terpenyl-Pyrrolizidine and Terpenyl-Imidazole Alkaloids from a Southern Australian Marine Sponge, Stelletta sp
    • El-Naggar, M.; Piggott, A.M.; Capon, R.J. Bistellettazines A-C and Bistellettazole A: New Terpenyl-Pyrrolizidine and Terpenyl-Imidazole Alkaloids from a Southern Australian Marine Sponge, Stelletta sp. Org. Lett. 2008, 10, 4247-4250.
    • (2008) Org. Lett. , vol.10 , pp. 4247-4250
    • El-Naggar, M.1    Piggott, A.M.2    Capon, R.J.3
  • 34
    • 0014591941 scopus 로고
    • N-Acylenamines from oxazolines. New route to 2-acetamidogylcals
    • Castagnoli, N.J. N-Acylenamines from oxazolines. New route to 2-acetamidogylcals. J. Org. Chem. 1969, 34, 3187-3189.
    • (1969) J. Org. Chem. , vol.34 , pp. 3187-3189
    • Castagnoli, N.J.1
  • 35
    • 0001581736 scopus 로고
    • Total synthesis of (±)-14-epicorynoline, (±)-corynoline, and (±)-6-oxocorynoline
    • Cushman, M.; Abbaspour, A.; Gupta, Y.P. Total synthesis of (±)-14-epicorynoline, (±)-corynoline, and (±)-6- oxocorynoline. J. Am. Chem. Soc. 1983, 105, 2873-2879.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2873-2879
    • Cushman, M.1    Abbaspour, A.2    Gupta, Y.P.3
  • 36
    • 33744477937 scopus 로고    scopus 로고
    • Divergent Structural Complexity from a Linear Reaction Sequence: Synthesis of Fused and Spirobicyclic γ-Lactams from Common Synthetic Precursors
    • Masse, C.E.; Ng, P.Y.; Fukase, Y.; Sanchez-Rosello, M.; Shaw, J.T. Divergent Structural Complexity from a Linear Reaction Sequence: Synthesis of Fused and Spirobicyclic γ-Lactams from Common Synthetic Precursors. J. Comb. Chem. 2006, 8, 293-296.
    • (2006) J. Comb. Chem. , vol.8 , pp. 293-296
    • Masse, C.E.1    Ng, P.Y.2    Fukase, Y.3    Sanchez-Rosello, M.4    Shaw, J.T.5
  • 37
    • 35048870516 scopus 로고    scopus 로고
    • Diastereoselective Synthesis of ã-Lactams by a One-Pot, Four-Component Reaction
    • Wei, J.; Shaw, J.T. Diastereoselective Synthesis of ã-Lactams by a One-Pot, Four-Component Reaction. Org. Lett. 2007, 9, 4077-4080.
    • (2007) Org. Lett. , vol.9 , pp. 4077-4080
    • Wei, J.1    Shaw, J.T.2
  • 38
    • 69449100084 scopus 로고    scopus 로고
    • One-Step Synthesis of Complex Nitrogen Heterocycles from Imines and Alkyl-Substituted Maleic Anhydrides
    • Tang, Y.; Fettinger, J.C.; Shaw, J.T. One-Step Synthesis of Complex Nitrogen Heterocycles from Imines and Alkyl-Substituted Maleic Anhydrides. Org. Lett. 2009, 11, 3802-3805.
    • (2009) Org. Lett. , vol.11 , pp. 3802-3805
    • Tang, Y.1    Fettinger, J.C.2    Shaw, J.T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.