메뉴 건너뛰기




Volumn 140, Issue 24, 2018, Pages 7462-7465

Divergent Synthesis of Pyrone Diterpenes via Radical Cross Coupling

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 85048843793     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.8b04891     Document Type: Article
Times cited : (69)

References (31)
  • 1
    • 84903169207 scopus 로고    scopus 로고
    • Total Synthesis of Diterpenoid Pyrones, Nalanthalide, Sesquicillin, Candelalides A-C, and Subglutinols A, B
    • Katoh, T. Total Synthesis of Diterpenoid Pyrones, Nalanthalide, Sesquicillin, Candelalides A-C, and Subglutinols A, B. Stud. Nat. Prod. Chem. 2014, 43, 1, 10.1016/B978-0-444-63430-6.00001-1
    • (2014) Stud. Nat. Prod. Chem. , vol.43 , pp. 1
    • Katoh, T.1
  • 2
    • 0031801643 scopus 로고    scopus 로고
    • Sesquicillin, an Inhibitor of Glucocorticoid Mediated Signal Transduction
    • Engel, B.; Erkel, G.; Anke, T.; Sterner, O. Sesquicillin, an Inhibitor of Glucocorticoid Mediated Signal Transduction. J. Antibiot. 1998, 51, 518, 10.7164/antibiotics.51.518
    • (1998) J. Antibiot. , vol.51 , pp. 518
    • Engel, B.1    Erkel, G.2    Anke, T.3    Sterner, O.4
  • 3
    • 31444433606 scopus 로고    scopus 로고
    • New Sesquicillins, Insecticidal Antiobiotics Produced by Albophoma sp. FKI-1778
    • Uchida, R.; Imasato, R.; Yamaguchi, Y.; Masuma, R.; Shiomi, K.; Tomoda, H.; Omura, S. New Sesquicillins, Insecticidal Antiobiotics Produced by Albophoma sp. FKI-1778. J. Antibiot. 2005, 58, 804, 10.1038/ja.2005.107
    • (2005) J. Antibiot. , vol.58 , pp. 804
    • Uchida, R.1    Imasato, R.2    Yamaguchi, Y.3    Masuma, R.4    Shiomi, K.5    Tomoda, H.6    Omura, S.7
  • 4
    • 0028845809 scopus 로고
    • Subglutinols A and B: Immunosuppressive Compounds from the Endophytic Fungus Fusarium subglutinans
    • Lee, J. C.; Lobkovsky, E.; Pliam, N. B.; Strobel, G.; Clardy, J. Subglutinols A and B: Immunosuppressive Compounds from the Endophytic Fungus Fusarium subglutinans. J. Org. Chem. 1995, 60, 7076, 10.1021/jo00127a001
    • (1995) J. Org. Chem. , vol.60 , pp. 7076
    • Lee, J.C.1    Lobkovsky, E.2    Pliam, N.B.3    Strobel, G.4    Clardy, J.5
  • 5
    • 84979788563 scopus 로고    scopus 로고
    • New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145
    • Kato, H.; Tsunematsu, Y.; Yamamoto, T.; Namiki, T.; Kishimoto, S.; Noguchi, H.; Watanabe, K. New natural products isolated from Metarhizium robertsii ARSEF 23 by chemical screening and identification of the gene cluster through engineered biosynthesis in Aspergillus nidulans A1145. J. Antibiot. 2016, 69, 561, 10.1038/ja.2016.54
    • (2016) J. Antibiot. , vol.69 , pp. 561
    • Kato, H.1    Tsunematsu, Y.2    Yamamoto, T.3    Namiki, T.4    Kishimoto, S.5    Noguchi, H.6    Watanabe, K.7
  • 7
    • 56949097895 scopus 로고    scopus 로고
    • New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation
    • Kikuchi, H.; Hoshi, T.; Kitayama, M.; Sekiya, M.; Katou, Y.; Ueda, K.; Kubohara, Y.; Sato, H.; Shimazu, M.; Kurata, S.; Oshima, Y. New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation. Tetrahedron 2009, 65, 469, 10.1016/j.tet.2008.11.014
    • (2009) Tetrahedron , vol.65 , pp. 469
    • Kikuchi, H.1    Hoshi, T.2    Kitayama, M.3    Sekiya, M.4    Katou, Y.5    Ueda, K.6    Kubohara, Y.7    Sato, H.8    Shimazu, M.9    Kurata, S.10    Oshima, Y.11
  • 9
    • 0037090967 scopus 로고    scopus 로고
    • An Efficient Stereoselective Total Synthesis of DL-Sesquicillin, a Glucocorticoid Antagonist
    • Zhang, F.; Danishefsky, S. J. An Efficient Stereoselective Total Synthesis of DL-Sesquicillin, a Glucocorticoid Antagonist. Angew. Chem., Int. Ed. 2002, 41, 1434, 10.1002/1521-3773(20020415)41:8<1434::AID-ANIE1434>3.0.CO;2-A
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1434
    • Zhang, F.1    Danishefsky, S.J.2
  • 10
    • 76949094024 scopus 로고    scopus 로고
    • Enantioselective Total Synthesis of Novel Diterpenoid Pyrones (+)-Sesquicillin and (-)-Nalanthalide from Fungal Fermentations
    • Oguchi, T.; Watanabe, K.; Abe, H.; Katoh, T. Enantioselective Total Synthesis of Novel Diterpenoid Pyrones (+)-Sesquicillin and (-)-Nalanthalide from Fungal Fermentations. Heterocycles 2010, 80, 229, 10.3987/COM-08-S(S)2
    • (2010) Heterocycles , vol.80 , pp. 229
    • Oguchi, T.1    Watanabe, K.2    Abe, H.3    Katoh, T.4
  • 12
    • 77955205246 scopus 로고    scopus 로고
    • Total Synthesis, Assignment of the Absolute Stereochemistry, and Structure-Activity Relationship Studies of Subglutinols A and B
    • Kim, H.; Baker, J. B.; Park, Y.; Park, H.-B.; DeArmond, P. D.; Kim, S. H.; Fitzgerald, M. C.; Lee, D.-S.; Hong, J. Total Synthesis, Assignment of the Absolute Stereochemistry, and Structure-Activity Relationship Studies of Subglutinols A and B. Chem.-Asian J. 2010, 5, 1902, 10.1002/asia.201000147
    • (2010) Chem. - Asian J. , vol.5 , pp. 1902
    • Kim, H.1    Baker, J.B.2    Park, Y.3    Park, H.-B.4    Dearmond, P.D.5    Kim, S.H.6    Fitzgerald, M.C.7    Lee, D.-S.8    Hong, J.9
  • 13
    • 80052190114 scopus 로고    scopus 로고
    • Enantioselective Total Synthesis of (-)-Subglutinols A and B: Potential Immunosuppressive Agents Isolated from a Microorganism
    • Kikuchi, T.; Mineta, M.; Ohtaka, J.; Matsumoto, N.; Katoh, T. Enantioselective Total Synthesis of (-)-Subglutinols A and B: Potential Immunosuppressive Agents Isolated from a Microorganism. Eur. J. Org. Chem. 2011, 2011, 5020, 10.1002/ejoc.201100517
    • (2011) Eur. J. Org. Chem. , vol.2011 , pp. 5020
    • Kikuchi, T.1    Mineta, M.2    Ohtaka, J.3    Matsumoto, N.4    Katoh, T.5
  • 14
    • 77954562085 scopus 로고    scopus 로고
    • Aiming for the Ideal Synthesis
    • Gaich, T.; Baran, P. S. Aiming for the Ideal Synthesis. J. Org. Chem. 2010, 75, 4657, 10.1021/jo1006812
    • (2010) J. Org. Chem. , vol.75 , pp. 4657
    • Gaich, T.1    Baran, P.S.2
  • 15
    • 84990060779 scopus 로고    scopus 로고
    • Radicals: Reactive Intermediates with Transitional Potential
    • Yan, M.; Lo, J. C.; Edwards, J. T.; Baran, P. S. Radicals: Reactive Intermediates with Transitional Potential. J. Am. Chem. Soc. 2016, 138, 12692, 10.1021/jacs.6b08856
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 12692
    • Yan, M.1    Lo, J.C.2    Edwards, J.T.3    Baran, P.S.4
  • 16
    • 85042490050 scopus 로고    scopus 로고
    • Total Synthesis of Complex Terpenoids Employing Radical Cascade Processes
    • Hung, K.; Hu, X.; Maimone, T. J. Total Synthesis of Complex Terpenoids Employing Radical Cascade Processes. Nat. Prod. Rep. 2018, 35, 174, 10.1039/C7NP00065K
    • (2018) Nat. Prod. Rep. , vol.35 , pp. 174
    • Hung, K.1    Hu, X.2    Maimone, T.J.3
  • 19
    • 0001147116 scopus 로고
    • Manganese (III)-Based Oxidative Free-Radical Cyclization Synthesis of (±)-Podocarpic Acid
    • Snider, B. B.; Mohan, R. M.; Kates, S. A. Manganese (III)-Based Oxidative Free-Radical Cyclization Synthesis of (±)-Podocarpic Acid. J. Org. Chem. 1985, 50, 3659, 10.1021/jo00219a054
    • (1985) J. Org. Chem. , vol.50 , pp. 3659
    • Snider, B.B.1    Mohan, R.M.2    Kates, S.A.3
  • 20
    • 0025752450 scopus 로고
    • Aspects of Manganese (III) - Promoted Oxidative Free Radical Cyclizations to Functionalized Bicyclic Systems
    • Zoretic, P. A.; Ramchandani, M.; Caspar, M. L. Aspects of Manganese (III)-Promoted Oxidative Free Radical Cyclizations to Functionalized Bicyclic Systems. Synth. Commun. 1991, 21, 915, 10.1080/00397919108019776
    • (1991) Synth. Commun. , vol.21 , pp. 915
    • Zoretic, P.A.1    Ramchandani, M.2    Caspar, M.L.3
  • 21
    • 7044286458 scopus 로고    scopus 로고
    • Manganese (III)-Based Oxidative Free-Radical Cyclizations
    • Snider, B. B. Manganese (III)-Based Oxidative Free-Radical Cyclizations. Chem. Rev. 1996, 96, 339, 10.1021/cr950026m
    • (1996) Chem. Rev. , vol.96 , pp. 339
    • Snider, B.B.1
  • 22
    • 0001620295 scopus 로고
    • Palladium-Catalyzed Decarboxylation-Dehydrogenation of Allyl β-Keto Carboxylates and Allyl Enol Carbonates as a Novel Synthetic Method for α-Substituted α,β-Unsaturated Ketones
    • Shimizu, I.; Tsuji, J. Palladium-Catalyzed Decarboxylation-Dehydrogenation of Allyl β-Keto Carboxylates and Allyl Enol Carbonates as a Novel Synthetic Method for α-Substituted α,β-Unsaturated Ketones. J. Am. Chem. Soc. 1982, 104, 5844, 10.1021/ja00385a075
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5844
    • Shimizu, I.1    Tsuji, J.2
  • 23
    • 0032501377 scopus 로고    scopus 로고
    • A Fully Synthetic Route to the Neurotrophic Illicinones by Sequential Aromatic Claisen Rearrangements
    • Pettus, T. R. R.; Chen, X.-T.; Danishefsky, S. J. A Fully Synthetic Route to the Neurotrophic Illicinones by Sequential Aromatic Claisen Rearrangements. J. Am. Chem. Soc. 1998, 120, 12684, 10.1021/ja982582e
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 12684
    • Pettus, T.R.R.1    Chen, X.-T.2    Danishefsky, S.J.3
  • 24
    • 84935097876 scopus 로고    scopus 로고
    • Total Synthesis of Oridamycins A and
    • Trotta, A. H. Total Synthesis of Oridamycins A and. Org. Lett. 2015, 17, 3358, 10.1021/acs.orglett.5b01629
    • (2015) Org. Lett. , vol.17 , pp. 3358
    • Trotta, A.H.1
  • 25
    • 0025976216 scopus 로고
    • Carbon-Carbon Bond Formation using Manganese (III) Acetate as an Electrochemical Mediator
    • For electrochemistry mediated addition of cyanoesters into olefins, see: See SI for optimization on the electrochemistry mediated polyene cyclization
    • For electrochemistry mediated addition of cyanoesters into olefins, see: Shundo, R.; Nishiguchi, I.; Matsubara, Y.; Hirashima, T. Carbon-Carbon Bond Formation using Manganese (III) Acetate as an Electrochemical Mediator. Tetrahedron 1991, 47, 831,. See SI for optimization on the electrochemistry mediated polyene cyclization 10.1016/S0040-4020(01)87071-X
    • (1991) Tetrahedron , vol.47 , pp. 831
    • Shundo, R.1    Nishiguchi, I.2    Matsubara, Y.3    Hirashima, T.4
  • 26
    • 82255186598 scopus 로고    scopus 로고
    • Palladium-Catalyzed Asymmetric Alkylation in the Synthesis of Cyclopentanoid and Cycloheptanoid Core Structures Bearing All-Carbon Quaternary Stereocenters
    • Hong, A. Y.; Bennett, N. B.; Krout, M. R.; Jensen, T.; Harned, A. M.; Stoltz, B. M. Palladium-Catalyzed Asymmetric Alkylation in the Synthesis of Cyclopentanoid and Cycloheptanoid Core Structures Bearing All-Carbon Quaternary Stereocenters. Tetrahedron 2011, 67, 10234, 10.1016/j.tet.2011.10.031
    • (2011) Tetrahedron , vol.67 , pp. 10234
    • Hong, A.Y.1    Bennett, N.B.2    Krout, M.R.3    Jensen, T.4    Harned, A.M.5    Stoltz, B.M.6
  • 27
    • 33947087984 scopus 로고
    • High Stereo- and Regioselectivities in the Transition Metal Catalyzed Epoxidations of Olefinic Alcohols by tert-Butyl Hydroperoxide
    • Sharpless, K. B.; Michaelson, R. C. High Stereo- and Regioselectivities in the Transition Metal Catalyzed Epoxidations of Olefinic Alcohols by tert-Butyl Hydroperoxide. J. Am. Chem. Soc. 1973, 95, 6136, 10.1021/ja00799a061
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6136
    • Sharpless, K.B.1    Michaelson, R.C.2
  • 28
    • 0017850469 scopus 로고
    • Synthetic Studies on Polyether Antibiotics. II. Stereocontrolled Syntheses of Epoxides of Bishomoallylic Alcohols
    • Fukuyama, T.; Vranesic, B.; Negri, D. P.; Kishi, Y. Synthetic Studies on Polyether Antibiotics. II. Stereocontrolled Syntheses of Epoxides of Bishomoallylic Alcohols. Tetrahedron Lett. 1978, 19, 2741, 10.1016/S0040-4039(01)94849-X
    • (1978) Tetrahedron Lett. , vol.19 , pp. 2741
    • Fukuyama, T.1    Vranesic, B.2    Negri, D.P.3    Kishi, Y.4
  • 30
    • 80051678538 scopus 로고    scopus 로고
    • TPAP-Catalyzed Direct Oxidation of Primary Alcohols to Carboxylic Acids through Stabilized Aldehyde Hydrates
    • Schmidt, A.-K. C.; Stark, C. B. W. TPAP-Catalyzed Direct Oxidation of Primary Alcohols to Carboxylic Acids through Stabilized Aldehyde Hydrates. Org. Lett. 2011, 13, 4164, 10.1021/ol2014335
    • (2011) Org. Lett. , vol.13 , pp. 4164
    • Schmidt, A.-K.C.1    Stark, C.B.W.2
  • 31
    • 6844254241 scopus 로고
    • Tandem Radical Approach to Linear Condensed Cyclopentanoids. Total Synthesis of (±)-Hirsutene
    • Curran, D. P.; Rakiewicz, D. M. Tandem Radical Approach to Linear Condensed Cyclopentanoids. Total Synthesis of (±)-Hirsutene. J. Am. Chem. Soc. 1985, 107, 1448, 10.1021/ja00291a077
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1448
    • Curran, D.P.1    Rakiewicz, D.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.