메뉴 건너뛰기




Volumn 2, Issue 6, 2000, Pages 639-649

Solution phase synthesis of libraries of polycyclic natural product analogues by cascade radical annulation: Synthesis of a 64-member library of mappicine analogues and a 48-member library of mappicine ketone analogues

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BIOLOGICAL FACTOR; KETONE; MAPPICINE;

EID: 0034321912     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc000032i     Document Type: Article
Times cited : (41)

References (42)
  • 1
    • 0033156688 scopus 로고    scopus 로고
    • Comprehensive survey of combinatorial library synthesis: 1998
    • (a) Dolle, R. E.; Nelson, K. H. Comprehensive Survey of Combinatorial Library Synthesis: 1998. J. Comb. Chem. 1999, 1, 235-282.
    • (1999) J. Comb. Chem. , vol.1 , pp. 235-282
    • Dolle, R.E.1    Nelson, K.H.2
  • 3
    • 33749872930 scopus 로고    scopus 로고
    • Multicomponent reactions (MCR). 1. Perspectives of multicomponent reactions and their libraries
    • Ugi, I. Multicomponent reactions (MCR). 1. Perspectives of Multicomponent Reactions and their Libraries. J. Prakt. Chem. Chem. Ztg. 1997, 339, 499-516.
    • (1997) J. Prakt. Chem. Chem. Ztg. , vol.339 , pp. 499-516
    • Ugi, I.1
  • 4
    • 0033549539 scopus 로고    scopus 로고
    • Polymer-supported synthesis of nonoligomeric natural products
    • Watson, C. Polymer-supported Synthesis of Nonoligomeric Natural Products. Angew. Chem., Int. Ed. 1999, 38, 1903-1908.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1903-1908
    • Watson, C.1
  • 5
    • 0001815816 scopus 로고    scopus 로고
    • Frontiers in organic synthesis: Introduction
    • (a) Wender, P. A. Frontiers in Organic Synthesis: Introduction. Chem. Rev. 1996, 96, 1-2.
    • (1996) Chem. Rev. , vol.96 , pp. 1-2
    • Wender, P.A.1
  • 6
    • 7044235263 scopus 로고    scopus 로고
    • Domino reactions in organic synthesis
    • (b) 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
  • 10
    • 0028337296 scopus 로고
    • Synthesis and anti-HSV activity of a-ring-deleted mappicine ketone analog
    • (a) Pendrak, I.; Barney, S.; Wittrock, R.; Lambert, D. M.; Kingsbury, W. D. Synthesis and Anti-HSV Activity of a-Ring-Deleted Mappicine Ketone Analog. J. Org. Chem. 1994, 59, 2623-2625.
    • (1994) J. Org. Chem. , vol.59 , pp. 2623-2625
    • Pendrak, I.1    Barney, S.2    Wittrock, R.3    Lambert, D.M.4    Kingsbury, W.D.5
  • 11
    • 0029036345 scopus 로고
    • Synthesis and anti-HSV activity of methylenedioxy mappicine ketone analogs
    • (b) Pendrak, I.; Wittrock, R.; Kingsbury, W. D. Synthesis and Anti-HSV Activity of Methylenedioxy Mappicine Ketone Analogs. J. Org. Chem. 1995, 60, 2912-2915.
    • (1995) J. Org. Chem. , vol.60 , pp. 2912-2915
    • Pendrak, I.1    Wittrock, R.2    Kingsbury, W.D.3
  • 12
    • 0030472098 scopus 로고    scopus 로고
    • Concise synthesis of mappicine ketone and (±)-mappicine
    • (a) Comins, D. L.; Sana, J. K. Concise Synthesis of Mappicine Ketone and (±)-Mappicine. J. Org. Chem. 1996, 61, 9623-9624.
    • (1996) J. Org. Chem. , vol.61 , pp. 9623-9624
    • Comins, D.L.1    Sana, J.K.2
  • 13
    • 0001630608 scopus 로고    scopus 로고
    • Heterocyclic and acyclic azadiene diels-alder reactions: Total synthesis of nothapodytine B
    • (b) Boger, D. L. Heterocyclic and Acyclic Azadiene Diels-Alder reactions: Total Synthesis of Nothapodytine B. J. Heterocycl. Chem. 1998, 35, 1003-1011.
    • (1998) J. Heterocycl. Chem. , vol.35 , pp. 1003-1011
    • Boger, D.L.1
  • 14
    • 0032542584 scopus 로고    scopus 로고
    • Total synthesis of nothapodytine B and (-)-mappicine
    • Boger, D. L.; Hong, J. Y. Total Synthesis of Nothapodytine B and (-)-Mappicine. J. Am. Chem. Soc. 1998, 120, 1218-1222.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1218-1222
    • Boger, D.L.1    Hong, J.Y.2
  • 15
    • 0033597166 scopus 로고    scopus 로고
    • A convergent total synthesis of mappicine ketone: A leading antiviral compound
    • Yadav, J. S.; Sarkar, S.; Chandrasekhar, S. A Convergent Total Synthesis of Mappicine Ketone: A Leading Antiviral Compound. Tetrahedron 1999, 55, 5449-5456.
    • (1999) Tetrahedron , vol.55 , pp. 5449-5456
    • Yadav, J.S.1    Sarkar, S.2    Chandrasekhar, S.3
  • 16
    • 0033581018 scopus 로고    scopus 로고
    • Enantioselective synthesis of (S)- and (R)-mappicines and their analogues
    • (e) Das, B.; Madhusudhan, P. Enantioselective Synthesis of (S)- and (R)-Mappicines and their Analogues. Tetrahedron 1999, 55, 7875-7880.
    • (1999) Tetrahedron , vol.55 , pp. 7875-7880
    • Das, B.1    Madhusudhan, P.2
  • 17
    • 0028021327 scopus 로고
    • Preparation of mappicine ketones from camptothecins: Chemistry of the camptothecin E ring
    • Fortunak, J. M. D.; Mastrocola, A. R.; Mellinger, M.; Wood, J. L. Preparation of Mappicine Ketones from Camptothecins: Chemistry of the Camptothecin E Ring. Tetrahedron Lett. 1994, 55, 5763-5764.
    • (1994) Tetrahedron Lett. , vol.55 , pp. 5763-5764
    • Fortunak, J.M.D.1    Mastrocola, A.R.2    Mellinger, M.3    Wood, J.L.4
  • 18
    • 0032576798 scopus 로고    scopus 로고
    • Two efficient methods for the conversion of camptothecin to mappicine ketone, an antiviral lead compound
    • (b) Das, B.; Madhusudhan, P.; Kashinatham, A. Two Efficient Methods for the Conversion of Camptothecin to Mappicine Ketone, an Antiviral Lead Compound. Tetrahedron Lett. 1998, 39, 431-432.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 431-432
    • Das, B.1    Madhusudhan, P.2    Kashinatham, A.3
  • 19
    • 0032474497 scopus 로고    scopus 로고
    • The first conversion of camptothecin to (S)-mappicine by an efficient chemoenzymatic method
    • Das, B.; Madhusudhan, P.; Kashinatham, A. The First Conversion of Camptothecin to (S)-Mappicine by an Efficient Chemoenzymatic Method. Bioorg. Med. Chem. Lett. 1998, 8, 1403-1406.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1403-1406
    • Das, B.1    Madhusudhan, P.2    Kashinatham, A.3
  • 20
    • 0000914975 scopus 로고    scopus 로고
    • Chemoenzymatic transformation of the natural antitumor alkaloid 20-O-acetylcamptothecin to mappicine ketone and (S)-mappicine
    • Das, B.; Madhusudhan, P.; Venkataiah, B. Chemoenzymatic Transformation of the Natural Antitumor Alkaloid 20-O-Acetylcamptothecin to Mappicine Ketone and (S)-Mappicine. J. Indian Chem. Soc. 1998, 75, 662-665.
    • (1998) J. Indian Chem. Soc. , vol.75 , pp. 662-665
    • Das, B.1    Madhusudhan, P.2    Venkataiah, B.3
  • 21
    • 0007660828 scopus 로고
    • New 4+1 radical annulations -a formal total synthesis of (±)-camptothecin
    • (a) Curran, D. P.; Liu, H. New 4+1 Radical Annulations -A Formal Total Synthesis of (±)-Camptothecin. J. Am. Chem. Soc. 1992, 114, 5863-5864.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5863-5864
    • Curran, D.P.1    Liu, H.2
  • 22
    • 33751141093 scopus 로고
    • Cascade radical reactions of isonitriles: A second-generation synthesis of (20S)-camptothecin, topotecan, irinotecan, and GI-147211C
    • (b) Curran, D. P.; Ko, S. B.; Josien, H. Cascade Radical Reactions of Isonitriles: A Second-Generation Synthesis of (20S)-Camptothecin, Topotecan, Irinotecan, and GI-147211C. Angew. Chem., Int. Ed. 1995, 34, 2683-2684.
    • (1995) Angew. Chem., Int. Ed. , vol.34 , pp. 2683-2684
    • Curran, D.P.1    Ko, S.B.2    Josien, H.3
  • 23
    • 0030603102 scopus 로고    scopus 로고
    • Tandem radical reactions of isonitriles with 2-pyridonyl and other aryl radicals: Scope and limitations, and a first generation synthesis of (±)-camptothecin
    • Curran, D. P.; Liu, H.; Josien, H.; Ko, S. B. Tandem Radical Reactions of Isonitriles with 2-Pyridonyl and other Aryl Radicals: Scope and Limitations, and a First Generation Synthesis of (±)-Camptothecin. Tetrahedron 1996, 52, 11385-11404.
    • (1996) Tetrahedron , vol.52 , pp. 11385-11404
    • Curran, D.P.1    Liu, H.2    Josien, H.3    Ko, S.B.4
  • 24
    • 0031934061 scopus 로고    scopus 로고
    • General synthetic approach to the (20S)-camptothecin family of antitumor agents by a regiocontrolled cascade radical cyclization of aryl isonitriles
    • Josien, H.; Ko, S. B.; Bom, D.; Curran, D. P. A General Synthetic Approach to the (20S)-Camptothecin Family of Antitumor Agents by a Regiocontrolled Cascade Radical Cyclization of Aryl Isonitriles. Chem. Eur. J. 1998, 4, 67-83.
    • (1998) Chem. Eur. J. , vol.4 , pp. 67-83
    • Josien, H.1    Ko, S.B.2    Bom, D.3    Curran, D.P.A.4
  • 25
    • 0344074659 scopus 로고    scopus 로고
    • 7-silyl-camptothecins (silatecans): A new family of camptothecin antitumor agents
    • (e) Josien, H.; Bom, D.; Curran, D. P.; Zheng, Y.-H.; Chou, T.-C. 7-Silyl-camptothecins (Silatecans): A New Family of Camptothecin Antitumor Agents. Bioorg. Med. Chem. Lett. 1997, 7, 3189-3295.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 3189-3295
    • Josien, H.1    Bom, D.2    Curran, D.P.3    Zheng, Y.-H.4    Chou, T.-C.5
  • 26
    • 0030839899 scopus 로고    scopus 로고
    • Synthesis of (S)-mappicine and mappicine ketone via radical reaction of isonitriles
    • Josien, H.; Curran, D. P. Synthesis of (S)-Mappicine and Mappicine Ketone via Radical Reaction of Isonitriles. Tetrahedron 1997, 53, 8881-8886.
    • (1997) Tetrahedron , vol.53 , pp. 8881-8886
    • Josien, H.1    Curran, D.P.2
  • 27
    • 0001580216 scopus 로고
    • A new synthetic route to (±)-strigol
    • Dailey, O. D. A New Synthetic Route to (±)-Strigol. J. Org. Chem. 1987, 52, 1984.
    • (1987) J. Org. Chem. , vol.52 , pp. 1984
    • Dailey, O.D.1
  • 28
    • 0039827338 scopus 로고    scopus 로고
    • Preparation of highly functionalized grignard reagents by an iodine - Magnesium exchange reaction and it's applications in solid-phase synthesis
    • (a) Boynard, L.; Rottländer, M.; Cahiez, G.; Knochel, P. Preparation of Highly Functionalized Grignard Reagents by an Iodine - Magnesium Exchange Reaction and it's Applications in Solid-Phase Synthesis. Angew. Chem., Int. Ed. 1998, 37, 1701.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1701
    • Boynard, L.1    Rottländer, M.2    Cahiez, G.3    Knochel, P.4
  • 29
    • 0002836067 scopus 로고    scopus 로고
    • Preparation of highly functionalized pyridylmagnesium reagents for the synthesis of polyfunctional pyridines
    • (b) Berillon, L.; Lepretre, A.; Turch, A.; Ple, P.; Queguiner, G.; Cahiez, G.; Knochel, P. Preparation of Highly Functionalized Pyridylmagnesium Reagents for the Synthesis of Polyfunctional Pyridines. Synlett 1998, 1359.
    • (1998) Synlett , pp. 1359
    • Berillon, L.1    Lepretre, A.2    Turch, A.3    Ple, P.4    Queguiner, G.5    Cahiez, G.6    Knochel, P.7
  • 30
    • 33845280673 scopus 로고
    • Synthesis and reactivity toward acyl chlorides and enones of the new highly functionalized copper reagents RCu (CN) ZnI
    • Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. Synthesis and Reactivity toward Acyl Chlorides and Enones of the New Highly Functionalized Copper Reagents RCu (CN) ZnI. J. Org. Chem. 1988, 53, 2393.
    • (1988) J. Org. Chem. , vol.53 , pp. 2393
    • Knochel, P.1    Yeh, M.C.P.2    Berk, S.C.3    Talbert, J.4
  • 31
    • 0010176851 scopus 로고
    • Chiral synthesis via organoboranes. 14. Selective reductions. 41. Diisopinocampheylchloroborane, an exceptionally efficient chiral reducing agent
    • Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. Chiral Synthesis via Organoboranes. 14. Selective Reductions. 41. Diisopinocampheylchloroborane, an Exceptionally Efficient Chiral Reducing Agent. J. Am. Chem. Soc. 1988, 110, 1539.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1539
    • Brown, H.C.1    Chandrasekharan, J.2    Ramachandran, P.V.3
  • 32
    • 0033574494 scopus 로고    scopus 로고
    • Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis
    • Linclau, B.; Singh, A. K.; Curran, D. P. Organic-Fluorous Phase Switches: A Fluorous Amine Scavenger for Purification in Solution Phase Parallel Synthesis. J. Org. Chem. 1999, 64, 2835.
    • (1999) J. Org. Chem. , vol.64 , pp. 2835
    • Linclau, B.1    Singh, A.K.2    Curran, D.P.3
  • 33
    • 85037500553 scopus 로고    scopus 로고
    • note
    • B = H or Me by this procedure since they were insoluble and were largely retained during the solid phase extraction.
  • 34
    • 0002297755 scopus 로고
    • Application of functionalized polymers in organic synthesis
    • (a) Akelah, A.: Sherrington. D. C. Application of Functionalized Polymers in Organic Synthesis. Chem. Rev. 1981, 81, 557.
    • (1981) Chem. Rev. , vol.81 , pp. 557
    • Akelah, A.1    Sherrington, D.C.2
  • 35
    • 0030777553 scopus 로고    scopus 로고
    • Functionalized polymers: Recent developments and new applications in synthetic organic chemistry
    • (b) Shuttleworth, S. J.; Allin, S. M.; Sharma. P. K. Functionalized Polymers: Recent Developments and New Applications in Synthetic Organic Chemistry. Synthesis 1997, 1217.
    • (1997) Synthesis , pp. 1217
    • Shuttleworth, S.J.1    Allin, S.M.2    Sharma, P.K.3
  • 36
    • 0011963165 scopus 로고
    • Polymeric reagents. 3. Poly[vinyl(pyridinium chlorochromate)]: A new recyclable oxidizing agent
    • Fréchet, J. M.; Warnock, J.: Farrall, M. J. Polymeric Reagents. 3. Poly[Vinyl(Pyridinium Chlorochromate)]: A New Recyclable Oxidizing Agent. J. Org. Chem. 1978, 43, 2618.
    • (1978) J. Org. Chem. , vol.43 , pp. 2618
    • Fréchet, J.M.1    Warnock, J.2    Farrall, M.J.3
  • 37
    • 0000424260 scopus 로고
    • Poly(vinylpyridinium dichromate): An inexpensive recyclable polymeric reagent
    • Fréchet, J. M.; Darling, P.: Farrall, M. J. Poly(Vinylpyridinium Dichromate): An Inexpensive Recyclable Polymeric Reagent. J. Org. Chem. 1981, 46, 1728.
    • (1981) J. Org. Chem. , vol.46 , pp. 1728
    • Fréchet, J.M.1    Darling, P.2    Farrall, M.J.3
  • 38
    • 33748719848 scopus 로고    scopus 로고
    • Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents
    • Caldarelli, M.; Habermann, J.; Ley. S. V. Clean Five-Step Synthesis of an Array of 1,2,3,4-Tetra-Substituted Pyrroles Using Polymer-Supported Reagents. J. Chem. Soc., Perkin Trans, 1 1999, 107.
    • (1999) J. Chem. Soc., Perkin Trans , vol.1 , pp. 107
    • Caldarelli, M.1    Habermann, J.2    Ley, S.V.3
  • 39
    • 0033612114 scopus 로고    scopus 로고
    • High-throughout purification of solution-phase periodinane mediated oxidation reactions utilizing a novel thiosulfate resin
    • Parlow, J. J.; Case, B. L.; South, M. S. High-Throughout Purification of Solution-Phase Periodinane Mediated Oxidation Reactions Utilizing a Novel Thiosulfate Resin. Tetrahedron 1999, 55, 6785.
    • (1999) Tetrahedron , vol.55 , pp. 6785
    • Parlow, J.J.1    Case, B.L.2    South, M.S.3
  • 40
    • 33748733929 scopus 로고    scopus 로고
    • Polymer supported perruthenate (psp): A new oxidant for clean organic synthesis
    • (a) Hinzen B.; Ley, S. V. Polymer Supported Perruthenate (PSP): A New Oxidant for Clean Organic Synthesis. J. Chem. Soc., Perkin. Tram. 1 1997, 1907.
    • (1997) J. Chem. Soc., Perkin. Tram. , vol.1 , pp. 1907
    • Hinzen, B.1    Ley, S.V.2
  • 41
    • 0031873305 scopus 로고    scopus 로고
    • Polymer supported perruthenate (PSP): Clean oxidation of primary alcohols to carbonyl compounds using oxygen as co-oxidant
    • (b) Hinzen, B.; Lenz, R.; Ley, S. V. Polymer Supported Perruthenate (PSP): Clean Oxidation of Primary Alcohols to Carbonyl Compounds Using Oxygen as Co-oxidant. Synthesis 1998, 977.
    • (1998) Synthesis , pp. 977
    • Hinzen, B.1    Lenz, R.2    Ley, S.V.3
  • 42
    • 33847799410 scopus 로고
    • Polymer supported reagents. Chromic acid on anion exchange resins. A simple and practical oxidation of alcohols to aldehydes and ketones
    • Cainelli, G.; Cardillo, G.; Orena, M.; Sandri, S. Polymer Supported Reagents. Chromic Acid on Anion Exchange Resins. A Simple and Practical Oxidation of Alcohols to Aldehydes and Ketones. J. Am. Chem. Soc. 1976, 98, 6737.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 6737
    • Cainelli, G.1    Cardillo, G.2    Orena, M.3    Sandri, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.