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Volumn 446, Issue 7134, 2007, Pages 404-408

Total synthesis of marine natural products without using protecting groups

Author keywords

[No Author keywords available]

Indexed keywords

AMBIQUINE H; FISCHERINDOLE I; FISCHERINDOLE U; HAPALINDOLE Q; HAPALINDOLE U; NATURAL PRODUCT; UNCLASSIFIED DRUG; WELWITINDOLINONE A;

EID: 33947602410     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature05569     Document Type: Article
Times cited : (423)

References (48)
  • 3
    • 0001144522 scopus 로고    scopus 로고
    • Wöhler, F. Ueber die Künstliche Bildung des Harnstoffe Poggendorfs. Ann. Phys. Chem. 12, 253-256 (1828).
    • Wöhler, F. Ueber die Künstliche Bildung des Harnstoffe Poggendorfs. Ann. Phys. Chem. 12, 253-256 (1828).
  • 4
    • 0033538379 scopus 로고    scopus 로고
    • molecular summits
    • Service
    • Service, R. F. Race for molecular summits. Science 285, 184-187 (1999).
    • (1999) Science , vol.285 , pp. 184-187
    • Race for, R.F.1
  • 5
    • 0025649186 scopus 로고
    • Organic synthesis-where now?
    • Seebach, D. Organic synthesis-where now? Angew. Chem. Int. Edn Engl. 29, 1320-1367 (1990).
    • (1990) Angew. Chem. Int. Edn Engl , vol.29 , pp. 1320-1367
    • Seebach, D.1
  • 8
    • 33751317736 scopus 로고    scopus 로고
    • Protecting group free synthesis
    • Hoffmann, R. W. Protecting group free synthesis. Synthesis 3531-3541 (2006).
    • (2006) Synthesis , vol.3531-3541
    • Hoffmann, R.W.1
  • 10
    • 11344292132 scopus 로고    scopus 로고
    • The role of natural product chemistry in drug discovery
    • Butler, M. S. The role of natural product chemistry in drug discovery. J. Nat. Prod. 67, 2141-2153 (2004).
    • (2004) J. Nat. Prod , vol.67 , pp. 2141-2153
    • Butler, M.S.1
  • 11
    • 33750464876 scopus 로고    scopus 로고
    • Small molecule natural products in the discovery of therapeutic agents: The synthesis connection
    • Wilson, R. M. & Danishefsky, S. J. Small molecule natural products in the discovery of therapeutic agents: the synthesis connection. J. Org. Chem. 71, 8329-8351 (2006).
    • (2006) J. Org. Chem , vol.71 , pp. 8329-8351
    • Wilson, R.M.1    Danishefsky, S.J.2
  • 13
    • 0027973653 scopus 로고
    • Welwitindolinones, unusual alkaloids from the blue-green algae Hapalosiphon welwitschii and Westiella intricate. Relationship to fischerindoles and hapalindoles
    • Stratmann, K. et al. Welwitindolinones, unusual alkaloids from the blue-green algae Hapalosiphon welwitschii and Westiella intricate. Relationship to fischerindoles and hapalindoles. J. Am. Chem. Soc. 116, 9935-9942 (1994).
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 9935-9942
    • Stratmann, K.1
  • 14
    • 0033866183 scopus 로고    scopus 로고
    • Biomimetic synthesis of alkaloids
    • Scholz, U. & Winterfeldt, E. Biomimetic synthesis of alkaloids. Nat. Prod. Rep. 17, 349-366 (2000).
    • (2000) Nat. Prod. Rep , vol.17 , pp. 349-366
    • Scholz, U.1    Winterfeldt, E.2
  • 15
    • 0023846718 scopus 로고
    • 12: Experiments concerning the origin of its molecular structure
    • 12: experiments concerning the origin of its molecular structure. Angew. Chem. Int. Edn Engl. 27, 5-39 (1988).
    • (1988) Angew. Chem. Int. Edn Engl , vol.27 , pp. 5-39
    • Eschenmoser, A.1
  • 16
    • 33748232292 scopus 로고
    • The enchanting alkaloids of Yuzuriha
    • Heathcock, C. H. The enchanting alkaloids of Yuzuriha. Angew. Chem. Int. Edn Engl. 31, 665-681 (1992).
    • (1992) Angew. Chem. Int. Edn Engl , vol.31 , pp. 665-681
    • Heathcock, C.H.1
  • 17
    • 0001598577 scopus 로고
    • Hapalindoles: New alkaloids from the blue-green alga Hapalosiphon fontinalis
    • Moore, R. E., Cheuk, C. & Patterson, G. M. L. Hapalindoles: new alkaloids from the blue-green alga Hapalosiphon fontinalis. J. Am. Chem. Soc. 106, 6456-6457 (1984).
    • (1984) J. Am. Chem. Soc , vol.106 , pp. 6456-6457
    • Moore, R.E.1    Cheuk, C.2    Patterson, G.M.L.3
  • 18
    • 33845282176 scopus 로고
    • Hapalindoles, antibacterial and antimycotic alkaloids from the cyanophyte Hapalosiphon fontinalis
    • Moore, R. E. et al. Hapalindoles, antibacterial and antimycotic alkaloids from the cyanophyte Hapalosiphon fontinalis. J. Org. Chem. 52, 1036-1043 (1987).
    • (1987) J. Org. Chem , vol.52 , pp. 1036-1043
    • Moore, R.E.1
  • 19
    • 0026606140 scopus 로고
    • Ambiguine isonitriles, fungicidal hapalindole-type alkaloids from three genera of blue-green algae belonging to the Stigonemataceae
    • Smitka, T. A. et al. Ambiguine isonitriles, fungicidal hapalindole-type alkaloids from three genera of blue-green algae belonging to the Stigonemataceae. J. Org. Chem. 57, 857-861 (1992).
    • (1992) J. Org. Chem , vol.57 , pp. 857-861
    • Smitka, T.A.1
  • 20
    • 33947363667 scopus 로고    scopus 로고
    • Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel
    • doi:10.1021/np060495r in the press, published online 13 January
    • Raveh, A. & Carmeli, S. Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel. J. Nat. Prod. doi:10.1021/np060495r (in the press); published online 13 January 2007.
    • (2007) J. Nat. Prod
    • Raveh, A.1    Carmeli, S.2
  • 21
    • 0025102581 scopus 로고
    • Synthetic studies of marine alkaloids hapalindoles. Part 3. Total synthesis of (±)-hapalindoles H and U
    • Muratake, H., Kumagami, H. & Natsume, M. Synthetic studies of marine alkaloids hapalindoles. Part 3. Total synthesis of (±)-hapalindoles H and U. Tetrahedron 46, 6351-6360 (1990).
    • (1990) Tetrahedron , vol.46 , pp. 6351-6360
    • Muratake, H.1    Kumagami, H.2    Natsume, M.3
  • 22
    • 33947605891 scopus 로고
    • Terpenes to terpenes. Stereo- and enantio-selective synthesis of (+)-α-elemene and a short route to a versatile diquinane chiron
    • Mehta, G. & Acharyulu, P. V. R. Terpenes to terpenes. Stereo- and enantio-selective synthesis of (+)-α-elemene and a short route to a versatile diquinane chiron. J. Chem. Soc. Chem. Commun. 2759-2760 (1994).
    • (1994) J. Chem. Soc. Chem. Commun , vol.2759-2760
    • Mehta, G.1    Acharyulu, P.V.R.2
  • 23
    • 2942650166 scopus 로고    scopus 로고
    • Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families
    • Baran, P. S. & Richter, J. M. Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families. J. Am. Chem. Soc. 126, 7450-7451 (2004).
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 7450-7451
    • Baran, P.S.1    Richter, J.M.2
  • 24
    • 13244269968 scopus 로고    scopus 로고
    • Direct coupling of pyrroles with carbonyl compounds: Short enantioselective synthesis of (S)-ketorolac
    • Baran, P. S., Richter, J. M. & Lin, D. W. Direct coupling of pyrroles with carbonyl compounds: short enantioselective synthesis of (S)-ketorolac. Angew. Chem. Int. Edn Engl. 44, 609-612 (2005).
    • (2005) Angew. Chem. Int. Edn Engl , vol.44 , pp. 609-612
    • Baran, P.S.1    Richter, J.M.2    Lin, D.W.3
  • 25
    • 22744442306 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling reactions in total synthesis
    • Nicolaou, K. C., Bulger, P. G. & Sarlah, D. Palladium-catalyzed cross-coupling reactions in total synthesis. Angew. Chem. Int. Edn Engl. 44, 4442-4489 (2005).
    • (2005) Angew. Chem. Int. Edn Engl , vol.44 , pp. 4442-4489
    • Nicolaou, K.C.1    Bulger, P.G.2    Sarlah, D.3
  • 26
    • 0000591888 scopus 로고
    • Synthesis of nitrogen heterocycles via palladium-catalyzed intramolecular cyclization
    • Larock, R. C. & Babu, S. Synthesis of nitrogen heterocycles via palladium-catalyzed intramolecular cyclization. Tetrahedr. Lett. 28, 5291-5294 (1987).
    • (1987) Tetrahedr. Lett , vol.28 , pp. 5291-5294
    • Larock, R.C.1    Babu, S.2
  • 27
    • 0001173339 scopus 로고
    • Palladium catalysed tandem cyclisation-anion capture processes. Part 1: Background and hydride ion capture by alkyl- and π-allyl-palladium species
    • Burns, B. et al. Palladium catalysed tandem cyclisation-anion capture processes. Part 1: Background and hydride ion capture by alkyl- and π-allyl-palladium species. Tetrahedr. Lett. 29, 4329-4332 (1988).
    • (1988) Tetrahedr. Lett , vol.29 , pp. 4329-4332
    • Burns, B.1
  • 28
    • 33750236967 scopus 로고
    • Palladacycles as structurally defined catalysts for the Heck olefination of chloro- and bromoarenes
    • Herrmann, W. A. et al. Palladacycles as structurally defined catalysts for the Heck olefination of chloro- and bromoarenes. Angew. Chem. Int. Edn Engl. 34, 1844-1848 (1995).
    • (1995) Angew. Chem. Int. Edn Engl , vol.34 , pp. 1844-1848
    • Herrmann, W.A.1
  • 29
    • 0033616118 scopus 로고    scopus 로고
    • Total synthesis of gypsetin, deoxybrevianamide E, brevianamide E, and tryprostatin B: Novel constructions of 2,3-disubstituted indoles
    • Schkeryantz, J. M., Woo, J. C. G., Siliphaivanth, P., Depew, K. M. & Danishefsky, S. J. Total synthesis of gypsetin, deoxybrevianamide E, brevianamide E, and tryprostatin B: Novel constructions of 2,3-disubstituted indoles. J. Am. Chem. Soc. 121, 11964-11975 (1999).
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 11964-11975
    • Schkeryantz, J.M.1    Woo, J.C.G.2    Siliphaivanth, P.3    Depew, K.M.4    Danishefsky, S.J.5
  • 31
    • 0002530666 scopus 로고    scopus 로고
    • Design constraints in practical syntheses of complex molecules: Current status, case studies with carbohydrates and alkaloids, and future perspectives
    • Hudlicky, T. Design constraints in practical syntheses of complex molecules: current status, case studies with carbohydrates and alkaloids, and future perspectives. Chem. Rev. 96, 3-30 (1996).
    • (1996) Chem. Rev , vol.96 , pp. 3-30
    • Hudlicky, T.1
  • 32
    • 27644566322 scopus 로고    scopus 로고
    • Enantioselective total synthesis of welwitindolinone A and fischerindoles I and G
    • Baran, P. S. & Richter, J. M. Enantioselective total synthesis of welwitindolinone A and fischerindoles I and G. J. Am. Chem. Soc. 127, 15394-15396 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 15394-15396
    • Baran, P.S.1    Richter, J.M.2
  • 33
    • 0000450576 scopus 로고
    • Selective oxidation of the side chain at C-3 of indoles
    • Oikawa, Y. &Yonemitsu, O. Selective oxidation of the side chain at C-3 of indoles. J. Org. Chem. 42, 1213-1216 (1977).
    • (1977) J. Org. Chem , vol.42 , pp. 1213-1216
    • Oikawa, Y.1    Yonemitsu, O.2
  • 34
    • 37049070835 scopus 로고
    • Reaction of xenon difluoride with indene in aqueous 1,2-dimethoxyethane and tetrahydrofuran
    • Shellhamer, D. F. et al. Reaction of xenon difluoride with indene in aqueous 1,2-dimethoxyethane and tetrahydrofuran. J. Chem. Soc. Perkin Trans. II, 401-403 (1991).
    • (1991) J. Chem. Soc. Perkin Trans , vol.2 , pp. 401-403
    • Shellhamer, D.F.1
  • 35
    • 33750444250 scopus 로고    scopus 로고
    • Baran, P. S. & Shenvi, R. A. Total synthesis of (±)- chartelline C. J. Am. Chem. Soc. 128, 14028-14029 (2006).
    • Baran, P. S. & Shenvi, R. A. Total synthesis of (±)- chartelline C. J. Am. Chem. Soc. 128, 14028-14029 (2006).
  • 37
    • 0026418434 scopus 로고
    • The atom economy - a search for synthetic efficiency
    • Trost, B. M. The atom economy - a search for synthetic efficiency. Science 254, 1471-1477 (1991).
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 40
    • 0004938188 scopus 로고
    • Systematic synthesis design. IV. Numerical codification of construction reactions
    • Hendrickson, J. B. Systematic synthesis design. IV. Numerical codification of construction reactions. J. Am. Chem. Soc. 97, 5784-5800 (1975).
    • (1975) J. Am. Chem. Soc , vol.97 , pp. 5784-5800
    • Hendrickson, J.B.1
  • 41
    • 0000918669 scopus 로고
    • Convergence, molecular complexity, and synthetic analysis
    • Bertz, S. H. Convergence, molecular complexity, and synthetic analysis. J. Am. Chem. Soc. 104, 5801-5803 (1982).
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 5801-5803
    • Bertz, S.H.1
  • 44
    • 0000458209 scopus 로고
    • Substrate-directable chemical reactions
    • Hoveyda, A. H., Evans, D. A. & Fu, G. C. Substrate-directable chemical reactions. Chem. Rev. 93, 1307-1370 (1993).
    • (1993) Chem. Rev , vol.93 , pp. 1307-1370
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 45
    • 0001815816 scopus 로고    scopus 로고
    • Frontiers in Organic Synthesis
    • Wender, P. A, ed
    • Wender, P. A. (ed.) Frontiers in Organic Synthesis. Chem. Rev. 96 (special issue), 1-600 (1996).
    • (1996) Chem. Rev , vol.96 , Issue.SPEC. ISSUE , pp. 1-600
  • 46
    • 0037846481 scopus 로고    scopus 로고
    • An enantioselective synthesis of FR182877 provides a chemical rationalization of its structure and affords multigram quantities of its direct precursor
    • Vanderwal, C. D., Vosburg, D. A., Weiler, S. & Sorensen, E. J. An enantioselective synthesis of FR182877 provides a chemical rationalization of its structure and affords multigram quantities of its direct precursor. J. Am. Chem. Soc. 125, 5393-5407 (2003).
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 5393-5407
    • Vanderwal, C.D.1    Vosburg, D.A.2    Weiler, S.3    Sorensen, E.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.