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Volumn 68, Issue 25, 2003, Pages 9728-9741

New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; DERIVATIVES; HYDROLYSIS; KETONES; PALLADIUM; POSITIVE IONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); VINYL RESINS;

EID: 0345097528     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034939p     Document Type: Article
Times cited : (77)

References (68)
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    • (b) Denmark, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, pp 751-784.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751-784
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  • 9
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    • For processes involving β-silyl or β-stannyl substituted dienones see: (a) Denmark, S. E.; Jones, T. K. J. Am. Chem. Soc. 1982, 104, 2642-2645.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 2642-2645
    • Denmark, S.E.1    Jones, T.K.2
  • 20
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    • Examples in which one of the two double bonds is embedded in an aromatic (indole) moiety are known, but it is not clear whether the reaction effectively occurs through a conrotatory 4π electrocyclic process: (c) Ishikura, M.; Imaizumi, K.; Katagiri, N. Heterocycles 2000, 53, 2201-2220.
    • (2000) Heterocycles , vol.53 , pp. 2201-2220
    • Ishikura, M.1    Imaizumi, K.2    Katagiri, N.3
  • 30
    • 0344127854 scopus 로고    scopus 로고
    • Moreover, compounds such as 5 are closely related to or are proline-specific Maillard compounds: (g) Chen, C.-W.; Lu, G.; Ho, C.-T. J. Agric. Food Chem. 1997, 45, 2996-2999.
    • (1997) J. Agric. Food Chem. , vol.45 , pp. 2996-2999
    • Chen, C.-W.1    Lu, G.2    Ho, C.-T.3
  • 31
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    • Examples of compounds having a structure closely related to 5 and 6 that have been used as intermediates in natural product synthesis: (h) Heathcock, C. H.; Norman, M. H.; Dickman, D. A. J. Org. Chem. 1990, 55, 798-811.
    • (1990) J. Org. Chem. , vol.55 , pp. 798-811
    • Heathcock, C.H.1    Norman, M.H.2    Dickman, D.A.3
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    • note
    • 3 solution.
  • 46
    • 0141855021 scopus 로고    scopus 로고
    • This is in accordance with the recent report by West who describes the need for more forcing conditions to effect the tandem Nazarov cyclization [4 + 3]-trapping of a cyclopenta-fused dienone: (a) Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.
    • (2003) Org. Lett. , vol.5 , pp. 2747-2750
    • Wang, Y.1    Schill, B.D.2    Arif, A.M.3    West, F.G.4
  • 47
    • 0034958711 scopus 로고    scopus 로고
    • Also, the same author has found that solvent trapping of photochemically generated pyran-4-ones does not occur in the case of cyclopenta-fused systems, again because of unacceptable levels of ring strain in the hypothetical oxyallyl zwitterion: (b) Fleming, M.; Fisher, P. V.; Gunawardena, G. U.; Jin, Y.; Zhang, C.; Zhang, W.; Arif, A. M.; West, F. G. Synthesis 2001, 1268-1274.
    • (2001) Synthesis , pp. 1268-1274
    • Fleming, M.1    Fisher, P.V.2    Gunawardena, G.U.3    Jin, Y.4    Zhang, C.5    Zhang, W.6    Arif, A.M.7    West, F.G.8
  • 48
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    • note
    • We tested γ-butyrolactone, α-angelicalactone, γ-valerolactone, and α-acetil-γ-butyrolactone under different experimental conditions (addition of the base to the lactone or lactone to the base, several molar ratios up to 4 equiv of base, reaction temperatures from -78 °C to room temperature, reaction times from 30 min to 20 h).
  • 51
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    • note
    • In the case of product 35, hydrolysis conditions must be carefully controlled in order to avoid the side hydrolysis of the cyclic vinyl ether moiety with subsequent opening of the seven-membered cycle. In this case (7E)-7-ethoxy-7,9-decadien-1-ol was recovered.
  • 54
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    • note
    • The oxidation was carried out on the crude mixtures obtained after workup of the N protection reactions. Although the overall yields were not satisfactory, we did not try at this stage to optimize them or evaluate other procedures to obtain these lactams.
  • 55
    • 0003480898 scopus 로고
    • Pergamon Press: Oxford, U.K.
    • 1H NMR spectrum. In particular, the two methyl groups resonate very close at 1.14 and 1.11 ppm which hampers the determination of their relative orientation by NOE studies. On the other hand, the signals of H4 (2.61 ppm) and H5 (2.86 ppm) are distinct but that of H4 in part overlaps with the signal (at 2.65 ppm) of a proton on C6. To distinguish between scalar and spatial interactions, a series of NOESY spectra were recorded by progressively changing the mixing time. In this way a NOESY cross-peak between H4 and H5 could be identified. Derome, A. E. Modern NMR Techniques for Chemistry Reserach; Pergamon Press: Oxford, U.K., 1987.
    • (1987) Modern NMR Techniques for Chemistry Reserach
    • Derome, A.E.1
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    • Farrugia, L.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.