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Volumn 50, Issue 9, 2009, Pages 1023-1025

Synthetic studies directed toward guianolides: an organoiron route to the 5,7,5 tricyclic ring system

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; CYCLOPROPANE DERIVATIVE; GAMMA LACTONE DERIVATIVE; GRIGNARD REAGENT; HETEROCYCLIC COMPOUND; IRON DERIVATIVE; SESQUITERPENE DERIVATIVE; VINYL DERIVATIVE;

EID: 58149501802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.051     Document Type: Article
Times cited : (15)

References (28)
  • 1
    • 58149520069 scopus 로고    scopus 로고
    • Fischer, N. H.; Olivier, E. J.; Fischer, H. D. Progress in the Chemistry of Organic Natural Products, 1979; Vol. 38.
    • Fischer, N. H.; Olivier, E. J.; Fischer, H. D. Progress in the Chemistry of Organic Natural Products, 1979; Vol. 38.
  • 2
    • 44649110874 scopus 로고    scopus 로고
    • Wiley-VCH, Germany pp 37-39
    • Breitmaier E. Terpenes (2006), Wiley-VCH, Germany pp 37-39
    • (2006) Terpenes
    • Breitmaier, E.1
  • 9
    • 85019044636 scopus 로고
    • For reviews of guianolide/pseudoguianolide syntheses see:. ApSimon J. (Ed), John Wiley & Sons, New York
    • For reviews of guianolide/pseudoguianolide syntheses see:. Heathcock C.H. In: ApSimon J. (Ed). The Total Synthesis of Natural Products Vol. 2 (1973), John Wiley & Sons, New York 197-558
    • (1973) The Total Synthesis of Natural Products , vol.2 , pp. 197-558
    • Heathcock, C.H.1
  • 12
    • 53749094941 scopus 로고    scopus 로고
    • For a recent review on the synthesis of guianolides with a trans-lactone moiety see:
    • For a recent review on the synthesis of guianolides with a trans-lactone moiety see:. Schall A., and Reiser O. Eur. J. Org. Chem. (2008) 2353-2364
    • (2008) Eur. J. Org. Chem. , pp. 2353-2364
    • Schall, A.1    Reiser, O.2
  • 13
    • 11844306006 scopus 로고    scopus 로고
    • Semi-syntheses of guianolides have been reported from photochemical rearrangement the naturally occurring terpene α-santonin:
    • Semi-syntheses of guianolides have been reported from photochemical rearrangement the naturally occurring terpene α-santonin:. Zhang W., Luo S., Fang F., Chen Q., Hu H., Jia X., and Zhai H. J. Am. Chem. Soc. 127 (2005) 18-19
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 18-19
    • Zhang, W.1    Luo, S.2    Fang, F.3    Chen, Q.4    Hu, H.5    Jia, X.6    Zhai, H.7
  • 21
    • 58149521936 scopus 로고    scopus 로고
    • note
    • 3) δ 0.81 (d, J = 9.0 Hz, 3H), 1.08 and 1.09 (2 × s, 9H total), 1.52-1.74 (m, 2H), 1.87-1.99 (m, 1H), 2.22-2.3.11 (m, 1H), 2.32-2.49 (m, 2H), 2.86-2.96 and 3.10-3.20 and 3.28-3.43 (m, 2H total), 4.06-4.19 and 4.32-4.39 (2 × m, 1H total), 5.24-5.50 (m, 2H), 5.81-5.92 (m, 1H), 7.35-7.49 (m, 6H), 7.65-7.76 (m, 4H).
  • 22
    • 0000353622 scopus 로고    scopus 로고
    • A similar selective reduction has been reported:
    • A similar selective reduction has been reported:. Davies H.M.L., and Doan B.D. J. Org. Chem. 63 (1998) 657-660
    • (1998) J. Org. Chem. , vol.63 , pp. 657-660
    • Davies, H.M.L.1    Doan, B.D.2
  • 23
    • 58149483412 scopus 로고    scopus 로고
    • note
    • +) m/z 450.2804).
  • 24
    • 58149512779 scopus 로고    scopus 로고
    • note
    • +) m/z 228.1576).
  • 27
    • 58149505614 scopus 로고    scopus 로고
    • The crystallographic data for 21 has been deposited with the CCDC (CCDC 690098). This data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retreiving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.ccdc.cam.ac.uk.
    • The crystallographic data for 21 has been deposited with the CCDC (CCDC 690098). This data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retreiving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.ccdc.cam.ac.uk.
  • 28
    • 58149512778 scopus 로고    scopus 로고
    • note
    • +) m/z 223.1334).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.