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Volumn 73, Issue 20, 2008, Pages 8109-8112

General, regiodefined access to α-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory Gorgonian lipid

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CHEMICAL REACTIONS; LITHIUM; RAW MATERIALS; SILANES;

EID: 53849103644     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015924     Document Type: Article
Times cited : (73)

References (74)
  • 39
    • 53849091183 scopus 로고    scopus 로고
    • Prepared in two steps from the parent butenolide (82% overall yield); see the Supporting Information of ref 13b for experimental details.
    • Prepared in two steps from the parent butenolide (82% overall yield); see the Supporting Information of ref 13b for experimental details.
  • 41
    • 0033804839 scopus 로고    scopus 로고
    • For a similar observation on the use of DMPU in a related reaction, see
    • For a similar observation on the use of DMPU in a related reaction, see: Xin, Z.; Zheng, G. Z.; Stewart, A. O. Synlett 2000, 1324-1326.
    • (2000) Synlett , pp. 1324-1326
    • Xin, Z.1    Zheng, G.Z.2    Stewart, A.O.3
  • 42
    • 0000073015 scopus 로고    scopus 로고
    • The precise mechanism of metal-halogen exchange reactions has yet to be settled; for recent studies see: (a) Jedlicka, B, Crabtree, R. H, Siegbahn, P. E. M. Organometallics 1997, 16, 6021-6023
    • The precise mechanism of metal-halogen exchange reactions has yet to be settled; for recent studies see: (a) Jedlicka, B.; Crabtree, R. H.; Siegbahn, P. E. M. Organometallics 1997, 16, 6021-6023.
  • 44
    • 53849130492 scopus 로고    scopus 로고
    • For alternative syntheses of 5i see: (a) Kvíèala, J.; Plocar, J.; Vlasáková, R.; Paleta, O.; Pelter, A. Synlett 1997, 986-988.
    • For alternative syntheses of 5i see: (a) Kvíèala, J.; Plocar, J.; Vlasáková, R.; Paleta, O.; Pelter, A. Synlett 1997, 986-988.
  • 52
    • 19944383454 scopus 로고    scopus 로고
    • Previously, 13 has been prepared from α-angelica lactone by isomerization and ensuing bromination-dehydrobromination in 20-52% yield over 2 steps: (a) Sorg, A.; Blank, F.; Brückner, R. Synlett 2005, 1286-1290.
    • Previously, 13 has been prepared from α-angelica lactone by isomerization and ensuing bromination-dehydrobromination in 20-52% yield over 2 steps: (a) Sorg, A.; Blank, F.; Brückner, R. Synlett 2005, 1286-1290.
  • 56
    • 0002557259 scopus 로고    scopus 로고
    • For the oxyfunctionalization of 2-silyloxyfurans and related compounds, see: a
    • For the oxyfunctionalization of 2-silyloxyfurans and related compounds, see: (a) Boukouvalas, J.; Lachance, N. Synlett 1998, 31-32.
    • (1998) Synlett , pp. 31-32
    • Boukouvalas, J.1    Lachance, N.2
  • 62
    • 0036796894 scopus 로고    scopus 로고
    • For some recent synthetic applications of vinylogous reactions of 2-silyloxyfurans with carbon electrophiles, see: a
    • For some recent synthetic applications of vinylogous reactions of 2-silyloxyfurans with carbon electrophiles, see: (a) Martin, S. F. Acc. Chem. Res. 2002, 35, 895-904.
    • (2002) Acc. Chem. Res , vol.35 , pp. 895-904
    • Martin, S.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.