메뉴 건너뛰기




Volumn 16, Issue 8, 2014, Pages 2162-2165

Total synthesis of (±)-cafestol: A late-stage construction of the furan ring inspired by a biosynthesis strategy

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; CAFESTOL; DITERPENE; FURAN; FURAN DERIVATIVE; GOLD CHLORIDE; GOLD DERIVATIVE; OCTANE;

EID: 84898978743     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500623w     Document Type: Article
Times cited : (56)

References (73)
  • 1
    • 0000502773 scopus 로고    scopus 로고
    • Diterpene Biosynthesis
    • Meth-Cohn, O. Barton, D. H. Nakanishi, K. Elsevier: Oxford
    • MacMillan, J.; Beale, M. H. Diterpene Biosynthesis. In Comprehensive Natural Products Chemistry; Meth-Cohn, O., Barton, D. H., Nakanishi, K., Eds.; Elsevier: Oxford, 1999; Vol. 2, pp 217-243.
    • (1999) Comprehensive Natural Products Chemistry , vol.2 , pp. 217-243
    • Macmillan, J.1    Beale, M.H.2
  • 15
    • 84898965050 scopus 로고    scopus 로고
    • Discovery and Development of Platensimycin and Platencin.
    • Genilloud, O. Vicente, F. RSC Publishing: Cambridge
    • Singh, S. B. Discovery and Development of Platensimycin and Platencin. In Drug Discovery from Natural Products; Genilloud, O.; Vicente, F., Eds.; RSC Publishing: Cambridge, 2012; p 249-277.
    • (2012) Drug Discovery from Natural Products , pp. 249-277
    • Singh, S.B.1
  • 20
    • 84899027582 scopus 로고    scopus 로고
    • The utilization of the classic Johnsons chiral acetal to initiate the cationic cyclization towards cafestol was attempted in our previous study, where the removal of the protecting group resulted in a moderate yield due to several unidentified side products; see
    • The utilization of the classic Johnsons chiral acetal to initiate the cationic cyclization towards cafestol was attempted in our previous study, where the removal of the protecting group resulted in a moderate yield due to several unidentified side products; see: Zhu, L.; Hong, R. Chin. J. Chem. 2013, 32, 114
    • (2013) Chin. J. Chem. , vol.32 , pp. 114
    • Zhu, L.1    Hong, R.2
  • 28
    • 5644252008 scopus 로고
    • Compounds cis - and trans - 9p were known in the literature (;); however, the full spectra data were not given. For the complete characterization, see the Supporting Information for details.
    • Compounds cis-and trans-9p were known in the literature (Banerjee, A. K.; Hurtado, H. E. Heterocycles 1981, 16, 613); however, the full spectra data were not given. For the complete characterization, see the Supporting Information for details.
    • (1981) Heterocycles , vol.16 , pp. 613
    • Banerjee, A.K.1    Hurtado, H.E.2
  • 30
    • 0001290261 scopus 로고
    • The Prins and Carbonyl Ene Reactions
    • Trost, B. M. Fleming, I. Pergamon Press: New York
    • Snider, B. B. The Prins and Carbonyl Ene Reactions. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, pp 527-561.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 36
    • 84899009455 scopus 로고    scopus 로고
    • 2AlCl was selected as the optimal promoter.
    • 2AlCl was selected as the optimal promoter.
  • 37
    • 84898971485 scopus 로고    scopus 로고
    • 2AlCl in the aldehyde-ene cyclizations, see pioneer works
    • 2AlCl in the aldehyde-ene cyclizations, see pioneer works
  • 50
    • 84882279077 scopus 로고    scopus 로고
    • For a very recent example in the synthesis of isosteviol where excellent regioselectivity was achieved when epoxide was applied as the initiator, see: Cherney, E. C.; Green, J. C.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 9019
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 9019
    • Cherney, E.C.1    Green, J.C.2    Baran, P.S.3
  • 60
    • 84899012354 scopus 로고    scopus 로고
    • CCDC 969986 (16) and CCDC 973471 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
    • CCDC 969986 (16) and CCDC 973471 (21) 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.