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Volumn 38, Issue 37, 1997, Pages 6537-6540

A β-lactone-based route to cyclopentanes via intramolecular allylsilane additions. An unexpected Friedel-Crafts alkylation

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; LACTONE DERIVATIVE; SILANE DERIVATIVE;

EID: 0030815185     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01529-3     Document Type: Article
Times cited : (12)

References (34)
  • 1
    • 0027175468 scopus 로고
    • For a recent review of β-lactones including their transformations, see: a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For more recent Lewis acid mediated transformations of β-lactones, see:
    • (1993) Synthesis , pp. 441-449
    • Pommier, A.1    Pons, J.-M.2
  • 8
    • 0001913118 scopus 로고
    • Apsimon, J., Ed; John Wiley&Sons: New York
    • Bacillariolides: Wang, R.; Shimizu, Y.; Steiner, J. R.; Clardy, J. C. J. Chem. Soc. Chem. Commun. 1993, 379-381. Brefeldins: For a review, see: Boeckman, R. K. Jr.; Goldstein, S. W. In Total Synthesis of Natural Products; Apsimon, J., Ed; John Wiley&Sons: New York, 1988; Vol. 17, pp. 29-41.
    • (1988) Total Synthesis of Natural Products , vol.17 , pp. 29-41
    • Boeckman R.K., Jr.1    Goldstein, S.W.2
  • 14
    • 0342660876 scopus 로고    scopus 로고
    • note
    • All new compounds reported herein exhibited spectroscopic and physical data consistent with their assigned structure.
  • 17
    • 0343497754 scopus 로고
    • Potassium bases led to greater quantities of rearranged allylic silylether (ref. 8b) and several unidentified by-products presumably derived from reaction of the β-lactone
    • b) Iio, H.; Ishii, M.; Tsukamoto, M.; Tokoroyama, Y. Tetrahedron Lett. 1988, 29, 5965-5968. Potassium bases led to greater quantities of rearranged allylic silylether (ref. 8b) and several unidentified by-products presumably derived from reaction of the β-lactone.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5965-5968
    • Iio, H.1    Ishii, M.2    Tsukamoto, M.3    Tokoroyama, Y.4
  • 21
    • 0343531118 scopus 로고    scopus 로고
    • note
    • 2: C, 72.49; H, 9.95. Found: C, 72.63; H, 10.00.
  • 22
    • 0343531117 scopus 로고    scopus 로고
    • note
    • +]: 168.1150. Found 168.1138.
  • 23
    • 84986437005 scopus 로고
    • The stereochemical assignment for bicylic lactone 16 is based on its IR carbonyl absorption, calculated (Macromodel V4.0 MM2*: Mohamadi, G.; Richards, N.G.J.; Guida, W. C.; Liskamp, R.; Caufield, C. Chang, T.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.) versus observed coupling constants, and previous conformational /stereochemical studies of δ-lactones and the structurally related iridiolactones, see:
    • (1990) J. Comput. Chem. , vol.11 , pp. 440
    • Mohamadi, G.1    Richards, N.G.J.2    Guida, W.C.3    Liskamp, R.4    Caufield, C.5    Chang, T.6    Hendrickson, T.7    Still, W.C.8
  • 26
    • 0024820534 scopus 로고
    • For an intramolecular cleavage of a β-lactone by a pendant benzylether which proceeds with inversion of configuration, see: Mead, K. T.; Yang, H. Tetrahedron Letters 1989, 30, 6829-6832.
    • (1989) Tetrahedron Letters , vol.30 , pp. 6829-6832
    • Mead, K.T.1    Yang, H.2
  • 27
    • 0342660868 scopus 로고    scopus 로고
    • note
    • 3 [M+H]: 275.1647. Found 275.1628.
  • 29
    • 0343095182 scopus 로고
    • Brauman, J. I.; Pandell, A. J. J. Am. Chem. Soc. 1967, 89, 5421-5424. For a recent example of a β-lactone participating in a Friedel-Crafts acylation, see:
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5421-5424
    • Brauman, J.I.1    Pandell, A.J.2
  • 34
    • 0026322486 scopus 로고
    • (no coupling constants are reported for these 3,4-disubstituted isochromans)
    • d) Singh, R.; Singh, R. P. D. Srivastava, J. N. J. Indian Chem. Soc. 1991, 68, 276-280. (no coupling constants are reported for these 3,4-disubstituted isochromans)
    • (1991) J. Indian Chem. Soc. , vol.68 , pp. 276-280
    • Singh, R.1    Singh, R.P.D.2    Srivastava, J.N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.