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Volumn 48, Issue 1, 2007, Pages 105-107

Facile access to 4-(1-alkynyl)-2(5H)-furanones by Sonogashira coupling of terminal acetylenes with β-tetronic acid bromide: efficient synthesis of cleviolide

Author keywords

Tetronic acid bromide; Cleviolide; Cross coupling; Heck alkynylation; Sonogashira reaction

Indexed keywords

ACETYLENE DERIVATIVE; CLEVIOLIDE; FURANONE DERIVATIVE; NATURAL PRODUCT; TERPENE; TETRONIC ACID DERIVATIVE;

EID: 33751405154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.156     Document Type: Article
Times cited : (46)

References (45)
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    • For a recent review on the use of cross-coupling reactions in total synthesis, see:
    • For a recent review on the use of cross-coupling reactions in total synthesis, see:. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442-4489
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 4442-4489
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  • 31
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    • For a synthesis of cleviolide from acyclic precursors by a novel palladium-tin cocatalysed tandem process, see:
    • For a synthesis of cleviolide from acyclic precursors by a novel palladium-tin cocatalysed tandem process, see:. Trost B.M., and McIntosh M.C. J. Am. Chem. Soc. 117 (1995) 7255-7256
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 7255-7256
    • Trost, B.M.1    McIntosh, M.C.2
  • 37
    • 0142196135 scopus 로고    scopus 로고
    • A couple of 4-(1-alkynyl)-(5H)-furanones have been prepared in modest overall yield (33-53%) by regioselective Sonogashira coupling of 1-alkynes with 3,4-dibromo-2(5H)-furanone and subsequent reductive removal of the 3-bromo substituent:
    • A couple of 4-(1-alkynyl)-(5H)-furanones have been prepared in modest overall yield (33-53%) by regioselective Sonogashira coupling of 1-alkynes with 3,4-dibromo-2(5H)-furanone and subsequent reductive removal of the 3-bromo substituent:. Bellina F., Falchi E., and Rossi R. Tetrahedron 59 (2003) 9091-9100
    • (2003) Tetrahedron , vol.59 , pp. 9091-9100
    • Bellina, F.1    Falchi, E.2    Rossi, R.3
  • 38
    • 0033536587 scopus 로고    scopus 로고
    • For the alkynylation of 5-alkyl-4-iodo-2(5H)-furanones, see:
    • For the alkynylation of 5-alkyl-4-iodo-2(5H)-furanones, see:. Ma S., Shi Z., and Yu Z. Tetrahedron 55 (1999) 12137-12148
    • (1999) Tetrahedron , vol.55 , pp. 12137-12148
    • Ma, S.1    Shi, Z.2    Yu, Z.3
  • 40
    • 0041728814 scopus 로고    scopus 로고
    • For some limitations of the Sonogashira reaction see: and references cited therein
    • For some limitations of the Sonogashira reaction see:. Negishi E., Qian M., Zeng F., Anastasia L., and Babinski D. Org. Lett. 5 (2003) 1597-1600 and references cited therein
    • (2003) Org. Lett. , vol.5 , pp. 1597-1600
    • Negishi, E.1    Qian, M.2    Zeng, F.3    Anastasia, L.4    Babinski, D.5
  • 41
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    • note
    • 3 193.0865).
  • 45
    • 33751397578 scopus 로고    scopus 로고
    • note
    • 3 180.0786).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.