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Volumn 48, Issue 37, 2009, Pages 6870-6874

Total synthesis of hirsutellone B

Author keywords

Antituberculosis; Cascade reactions; Natural product; Total synthesis

Indexed keywords

ANTITUBERCULOSIS; CASCADE REACTIONS; FUNGAL METABOLITES; LEWIS ACID; NATURAL PRODUCT; TOTAL SYNTHESIS; TRIMETHYLSILYL;

EID: 69549126522     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903382     Document Type: Article
Times cited : (99)

References (28)
  • 8
    • 60849120481 scopus 로고    scopus 로고
    • For previous studies toward the total synthesis of hirsutellones, see: a) S. D. Tilley, K. P. Reber, E. J. Sorensen, Org. Lett. 2009, 11, 701-703;
    • (2009) Org. Lett. , vol.11 , pp. 701-703
    • Tilley, S.D.1    Reber, K.P.2    Sorensen, E.J.3
  • 13
    • 22144459070 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4212-4215.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4212-4215
  • 14
    • 70349952509 scopus 로고    scopus 로고
    • 4] as a catalyst
    • 4] as a catalyst.
  • 16
    • 70349969931 scopus 로고    scopus 로고
    • CCDC 736469 (p-bromophenyl carbamate 12) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 736469 (p-bromophenyl carbamate 12) contains 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.
  • 21
    • 70349950702 scopus 로고    scopus 로고
    • The isomeric O-carboxymethylated compound was also isolated as a minor product (20% yield) in this reaction
    • The isomeric O-carboxymethylated compound was also isolated as a minor product (20% yield) in this reaction.
  • 23
    • 70349968202 scopus 로고    scopus 로고
    • CCDC 736468 (diol 16) contains the supplementary crystallo-graphic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC 736468 (diol 16) contains the supplementary crystallo-graphic 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.
  • 24
    • 70349955015 scopus 로고    scopus 로고
    • The corresponding decarboxymethylation compound (1,4-dike- tone 18 a, not shown) was also observed as a side product in this reaction. The likely formation of imine moieties at the two carbonyl sites of substrate 18 is reversible under the reaction conditions (i.e. H2O), thus allowing the eventual generation of the product (i.e. 1b). An alternative mechanism may involve initial attack of NH3 at the C2' carbonyl group and subsequent ring closure.
    • The corresponding decarboxymethylation compound (1,4-dike- tone 18 a, not shown) was also observed as a side product in this reaction. The likely formation of imine moieties at the two carbonyl sites of substrate 18 is reversible under the reaction conditions (i.e. H2O), thus allowing the eventual generation of the product (i.e. 1b). An alternative mechanism may involve initial attack of NH3 at the C2' carbonyl group and subsequent ring closure.
  • 28
    • 33750977591 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7134-7186


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.