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Volumn 3, Issue 26, 2001, Pages 4189-4192

Application of Lewis acid catalyzed tropone [6+4] cycloadditions to the synthesis of the core of CP-225,917

Author keywords

[No Author keywords available]

Indexed keywords

ACID; DRUG DERIVATIVE; ENZYME INHIBITOR; MALEIC ANHYDRIDE; PHOMOIDRIDE A; SQUALENE SYNTHASE; TROPOLONE; TROPONE;

EID: 0035961028     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016814h     Document Type: Article
Times cited : (66)

References (36)
  • 5
    • 0032546305 scopus 로고    scopus 로고
    • For related modifications of tropylium [6+4] adducts, see: (a) Rigby, J. H.; Fales, K. R. Tetrahedron Lett. 1998, 39, 1525.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1525
    • Rigby, J.H.1    Fales, K.R.2
  • 18
    • 0000535514 scopus 로고
    • Ito, S.; Sakan, K.; Fujise, Y. Tetrahedron Lett. 1970, 11, 2873. Ito et al. reported that reaction of tropone and cyclopentadiene in the presence of pTsOH afforded a 65% yield of 11 and a 15% yield of a mixture of [4+2] adducts, although the solvent, temperature, and amount of catalyst were not specified. We have found that use of 10% pTsOH in toluene afforded a 40% yield of 11 along with 38% of the [4+2] adduct, 12.
    • (1970) Tetrahedron Lett. , vol.11 , pp. 2873
    • Ito, S.1    Sakan, K.2    Fujise, Y.3
  • 20
    • 0001556437 scopus 로고    scopus 로고
    • Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382 . For a thermal version using a catalytic amount of chromium, see: Rigby, J. H.; Fiedler, C. J. Org. Chem. 1997, 62, 6106.
    • (1997) J. Org. Chem. , vol.62 , pp. 6106
    • Rigby, J.H.1    Fiedler, C.2
  • 23
    • 0001592335 scopus 로고    scopus 로고
    • 2-Trimethylsilyloxycyclopentadiene and 2-triethylsilyloxy-cyclopentadiene were prepared by silylation of 2-cyclopentenone with the corresponding silyl triflates and triethylamine. See: Plenio, H.; Aberle, C. Organometallics 1997, 16, 5950.
    • (1997) Organometallics , vol.16 , pp. 5950
    • Plenio, H.1    Aberle, C.2
  • 24
    • 0042220528 scopus 로고    scopus 로고
    • note
    • "Even" or "odd" regioselectivity in this case refers to the number of atoms along the shortest path between the functional groups in the cycloadduct.
  • 25
    • 33845555520 scopus 로고
    • Tropones 16, 18, and 20 were prepared by rhodium acetate catalyzed reaction of ethyl diazoacetate with anisole to give three cycloheptatrienes, which may be separated by chromatography and individually oxidized with bromine to afford the tropones. See: (a) Garst, M. E.; Roberts, V. A. J. Org. Chem. 1982, 47, 2188.
    • (1982) J. Org. Chem. , vol.47 , pp. 2188
    • Garst, M.E.1    Roberts, V.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.