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Volumn 48, Issue 29, 2009, Pages 5366-5368

Macrocyclization by nickel-catalyzed, ester-promoted, epoxide-alkyne reductive coupling: Total synthesis of (-)-gloeosporone

Author keywords

C C coupling; Cyclization; Nickel; Reductive coupling; Total synthesis

Indexed keywords

C-C BOND FORMATION; C-C COUPLING; MACRO-CYCLIZATION; NOVEL STRATEGIES; PHOSPHINE COMPLEX; REDUCTIVE COUPLING; REDUCTIVE COUPLINGS; TITLE COMPOUNDS; TOTAL SYNTHESIS;

EID: 70349900286     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902079     Document Type: Article
Times cited : (27)

References (40)
  • 2
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    • Ring-closing metathesis: a A. Gradillas, J. Perez-Castells, Angew. Chem. 2006, 118, 6232;
    • Ring-closing metathesis: a) A. Gradillas, J. Perez-Castells, Angew. Chem. 2006, 118, 6232;
  • 4
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    • C-H oxidation: b K. J. Fraunhoffer, N. Prabagaran, L. E. Sirois, M. C. White, J. Am. Chem. Soc. 2006, 128, 9032;
    • C-H oxidation: b) K. J. Fraunhoffer, N. Prabagaran, L. E. Sirois, M. C. White, J. Am. Chem. Soc. 2006, 128, 9032;
  • 5
    • 27644464046 scopus 로고    scopus 로고
    • nickel-mediated reactions: c K. Namba, Y. Kishi, J. Am. Chem. Soc. 2005, 127, 15382.
    • nickel-mediated reactions: c) K. Namba, Y. Kishi, J. Am. Chem. Soc. 2005, 127, 15382.
  • 25
    • 9644260362 scopus 로고    scopus 로고
    • We have observed the directing of regioselectivity in nickel-catalyzed coupling reactions of alkynes by a similarly positioned alkene: a K. M. Miller, T. F. Jamison, J. Am. Chem. Soc. 2004, 126, 15342;
    • We have observed the directing of regioselectivity in nickel-catalyzed coupling reactions of alkynes by a similarly positioned alkene: a) K. M. Miller, T. F. Jamison, J. Am. Chem. Soc. 2004, 126, 15342;
  • 34
    • 0000781078 scopus 로고    scopus 로고
    • 2: M. Rozema, A. Sidduri, P. Knochel, J. Org. Chem. 1992, 57, 1956.
    • 2: M. Rozema, A. Sidduri, P. Knochel, J. Org. Chem. 1992, 57, 1956.
  • 35
    • 70349947698 scopus 로고    scopus 로고
    • This ketone also undergoes high yielding and highly site-selective soft enolization at C4-C5 Et3SiOTf, Et3N, 90% yield, Elaboration of this enolsilane to gloeosporone by Rubottom oxidation was unsuccessful
    • 3N, 90% yield). (Elaboration of this enolsilane to gloeosporone by Rubottom oxidation was unsuccessful).
  • 37
    • 34547230641 scopus 로고    scopus 로고
    • for a recent use of Bredereck's reagent in target-oriented synthesis, see: b J. Peng, D. L. J. Clive, Org. Lett. 2007, 9, 2939.
    • for a recent use of Bredereck's reagent in target-oriented synthesis, see: b) J. Peng, D. L. J. Clive, Org. Lett. 2007, 9, 2939.
  • 38
    • 70349936041 scopus 로고    scopus 로고
    • 1H NMR spectral analysis of crude 11 (the NMR yield of 11 was >95%).
    • 1H NMR spectral analysis of crude 11 (the NMR yield of 11 was >95%).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.