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Volumn 47, Issue 38, 2006, Pages 6817-6820

Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

Author keywords

Cyclopropene; Dichlorocyclopropane; Furan; Furanosesquiterpene; Pallescensin A; Wieland Miescher ketone

Indexed keywords

CARBENOID; DECALONE; ESTER DERIVATIVE; FURAN DERIVATIVE; KETONE; PALLESCENSIN A; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33747190017     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.068     Document Type: Article
Times cited : (31)

References (37)
  • 2
    • 0005755655 scopus 로고
    • For a comprehensive review of earlier work in the area see:
    • For a comprehensive review of earlier work in the area see:. Hikino H., and Konno C. Heterocycles 4 (1976) 817-870
    • (1976) Heterocycles , vol.4 , pp. 817-870
    • Hikino, H.1    Konno, C.2
  • 3
    • 23944453831 scopus 로고    scopus 로고
    • For more recent surveys of sesquiterpene natural products that include coverage of furan-containing systems see: and earlier articles in this series
    • For more recent surveys of sesquiterpene natural products that include coverage of furan-containing systems see:. Fraga B.M. Nat. Prod. Rep. 22 (2005) 465-486 and earlier articles in this series
    • (2005) Nat. Prod. Rep. , vol.22 , pp. 465-486
    • Fraga, B.M.1
  • 5
    • 0004499722 scopus 로고    scopus 로고
    • Müller and Pautex (Müller, P.; Pautex, N. Helv. Chim. Acta 1988, 71, 1630-1637) have shown that the dichlorocarbene adducts of several 9-alkoxyphenanthracenes undergo base-induced conversions into furans but such protocols have not been applied more broadly, especially to enolizable ketones and for the purposes of the synthesis of natural products.
  • 6
    • 33744737931 scopus 로고    scopus 로고
    • For other examples of the use of gem-dihalogenocyclopropanes as starting materials in natural products synthesis, see: and references cited therein
    • For other examples of the use of gem-dihalogenocyclopropanes as starting materials in natural products synthesis, see:. Stanislawski P.C., Willis A.C., and Banwell M.G. Org. Lett. 8 (2006) 2143-2146 and references cited therein
    • (2006) Org. Lett. , vol.8 , pp. 2143-2146
    • Stanislawski, P.C.1    Willis, A.C.2    Banwell, M.G.3
  • 27
    • 33747162318 scopus 로고    scopus 로고
    • note
    • w = 0.0425, S = 1.0787. Atomic coordinates, bond lengths and angles, and displacement parameters have been deposited at the Cambridge Crystallographic Data Centre (CCDC reference number 607640). These data can be obtained free-of-charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
  • 30
    • 0002576061 scopus 로고
    • For a discussion of the methods available for the generation of dihalocarbenes see:. Halton B. (Ed), JAI Press, London
    • For a discussion of the methods available for the generation of dihalocarbenes see:. Banwell M.G., and Reum M.E. In: Halton B. (Ed). Advances in Strain in Organic Chemistry Vol. 1 (1991), JAI Press, London 19-64
    • (1991) Advances in Strain in Organic Chemistry , vol.1 , pp. 19-64
    • Banwell, M.G.1    Reum, M.E.2
  • 31
    • 33747151183 scopus 로고    scopus 로고
    • note
    • f = 0.4) afforded the cis-isomer of compound 1 (6 mg, 5%) as a clear, colorless oil.
  • 33
    • 33747155742 scopus 로고    scopus 로고
    • note
    • Compounds 14 and 15 were readily prepared by standard methods involving, in the second step, phase-transfer-generated dichlorocarbene addition to the methyl or ethyl enol ether derived from 1-tetralone.
  • 37
    • 2942718037 scopus 로고
    • We have observed that the dichlorocarbene adducts of certain other alkyl enol ethers undergo seemingly quite distinct elimination processes on treatment with potassium tert-butoxide in THF. See, for example
    • We have observed that the dichlorocarbene adducts of certain other alkyl enol ethers undergo seemingly quite distinct elimination processes on treatment with potassium tert-butoxide in THF. See, for example,. Banwell M.G., Gable R.W., Halton B., and Phyland J.R. Aust. J. Chem. 47 (1994) 1879-1884
    • (1994) Aust. J. Chem. , vol.47 , pp. 1879-1884
    • Banwell, M.G.1    Gable, R.W.2    Halton, B.3    Phyland, J.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.