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Volumn , Issue 32, 2008, Pages 5379-5382

Synthetic studies towards guaianolide sesquiterpene lactones

Author keywords

Chemoselectivity; Domino reaction; Guaianolides; Multicomponent reactions; Natural products

Indexed keywords


EID: 57349085748     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800825     Document Type: Article
Times cited : (14)

References (24)
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    • and previous reports in this series
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    • and previous reports in this series
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    • Isolation of 1a: a F. Bohlmann, C. Zdero, R. M. King, H. Robinson, Phytochemistry 1984, 23, 1187-1188;
    • Isolation of 1a: a) F. Bohlmann, C. Zdero, R. M. King, H. Robinson, Phytochemistry 1984, 23, 1187-1188;
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    • of 1b: b A. Ortega, R. A. Toscano, E. Maldonado, Phytochemistry 1998, 49, 1085-1090;
    • of 1b: b) A. Ortega, R. A. Toscano, E. Maldonado, Phytochemistry 1998, 49, 1085-1090;
  • 5
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    • of 2: c F. Bohlmann, C. Zdero, R. M. King, H. Robinson, Phytochemistry 1989, 28, 517-526.
    • of 2: c) F. Bohlmann, C. Zdero, R. M. King, H. Robinson, Phytochemistry 1989, 28, 517-526.
  • 7
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    • For recent examples involving compounds 1 or 2, see: a B. Siedle, A. J. García-Piñeres, R. Murillo, J. Schulte-Mönting, V. Castro, P. Rüngeler, C. A. Klaas, F. B. Da Costa, W. Kisiel, I. Merfort, J. Med. Chem. 2004, 47, 6042-6054;
    • For recent examples involving compounds 1 or 2, see: a) B. Siedle, A. J. García-Piñeres, R. Murillo, J. Schulte-Mönting, V. Castro, P. Rüngeler, C. A. Klaas, F. B. Da Costa, W. Kisiel, I. Merfort, J. Med. Chem. 2004, 47, 6042-6054;
  • 11
    • 84890597202 scopus 로고    scopus 로고
    • For recent monographs, see: a, Eds, J. Zhu, H. Bienaymé, Wiley-VCH, Weinheim
    • For recent monographs, see: a) Multicomponent Reactions (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005;
    • (2005) Multicomponent Reactions
  • 12
    • 84890766709 scopus 로고    scopus 로고
    • Eds, L. F. Tietze, G. Brasche, K. M. Gericke, Wiley-VCH, Weinheim
    • b) Domino Reactions in Organic Synthesis (Eds.: L. F. Tietze, G. Brasche, K. M. Gericke), Wiley-VCH, Weinheim, 2006.
    • (2006) Domino Reactions in Organic Synthesis
  • 14
    • 45849122883 scopus 로고    scopus 로고
    • For recent selected examples, see: a
    • For recent selected examples, see: a) J. Isaacson, M. Loo, Y. Kobayashi, Org. Lett. 2008, 10, 1461-1463;
    • (2008) Org. Lett , vol.10 , pp. 1461-1463
    • Isaacson, J.1    Loo, M.2    Kobayashi, Y.3
  • 18
    • 34250701386 scopus 로고    scopus 로고
    • CCDC-620411 (for 4) and -697454 [for 7 co-crystal of the two major diastereomers, contain the supplementary crystallographic data for this paper
    • CCDC-620411 (for 4) and -697454 [for 7 (co-crystal of the two major diastereomers)] contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
    • These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
  • 19
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    • This unusual reactivity of NaBH4 with β-hydroxy esters has previously been observed, though not fully rationalized, see: a N. Finch, L. D. Vecchia, J. J. Fitt, R. Stephani, I. Vlattas, J. Org. Chem. 1973, 38, 4412-4424;
    • 4 with β-hydroxy esters has previously been observed, though not fully rationalized, see: a) N. Finch, L. D. Vecchia, J. J. Fitt, R. Stephani, I. Vlattas, J. Org. Chem. 1973, 38, 4412-4424;
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    • Five chemical operations if the re-esterification of a part of the crude material of the MARDi cascade is included
    • Five chemical operations if the re-esterification of a part of the crude material of the MARDi cascade is included.
  • 24
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    • The commercially available β-oxo ester 3 is derived from dimethyl adipate (Dieckmann cyclization), whereas the aldehyde 6 is obtained either from cyclohexene or adipaldehyde according to a one-pot protocol: E. D. Bergmann, A. Becker, J. Am. Chem. Soc. 1959, 81, 221-225, and references cited therein.
    • The commercially available β-oxo ester 3 is derived from dimethyl adipate (Dieckmann cyclization), whereas the aldehyde 6 is obtained either from cyclohexene or adipaldehyde according to a one-pot protocol: E. D. Bergmann, A. Becker, J. Am. Chem. Soc. 1959, 81, 221-225, and references cited therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.