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Volumn 69, Issue 11, 2004, Pages 3719-3725

Radical and palladium-catalyzed cyclizations to cyclobutenes: An entry to the BCD ring system of penitrem D

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CATALYSIS; FREE RADICALS; STEREOCHEMISTRY;

EID: 2442666555     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049873s     Document Type: Article
Times cited : (25)

References (40)
  • 6
    • 0011204990 scopus 로고    scopus 로고
    • Zard, S. Z., Ed.; Jai Press: Stamford, CT
    • We use here the "radical/polar crossover" terminology of Murphy, but such reactions are also called by other names such as "cascade radical/ionic reactions". Bashir, N.; Patro, B.; Murphy, J. A. Advances In Free Radical Chemistry; Zard, S. Z., Ed.; Jai Press: Stamford, CT, 1999; Vol. 2, pp 123-150.
    • (1999) Advances in Free Radical Chemistry , vol.2 , pp. 123-150
    • Bashir, N.1    Patro, B.2    Murphy, J.A.3
  • 7
    • 85039535136 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Pittsburgh
    • (a) Nagashima, T. Ph.D. Thesis, University of Pittsburgh, 1999.
    • (1999)
    • Nagashima, T.1
  • 8
    • 85039524018 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Pittsburgh
    • (b) Rivkin, A. Ph.D. Thesis, University of Pittsburgh, 2001.
    • (2001)
    • Rivkin, A.1
  • 12
    • 0000315424 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
    • (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 779-831.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 779-831
    • Curran, D.P.1
  • 15
    • 0042789931 scopus 로고
    • For example, the ketone group of cyclobutanones has often been used in radical cyclization reactions: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Cyclizations to methylene cyclobutanes are also known: Zhang, W.; Dowd, P. Tetrahedron Lett. 1995, 36, 8539-8542.
    • (1993) Chem. Rev. , vol.93 , pp. 2091-2115
    • Dowd, P.1    Zhang, W.2
  • 16
    • 0028866090 scopus 로고
    • For example, the ketone group of cyclobutanones has often been used in radical cyclization reactions: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Cyclizations to methylene cyclobutanes are also known: Zhang, W.; Dowd, P. Tetrahedron Lett. 1995, 36, 8539-8542.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8539-8542
    • Zhang, W.1    Dowd, P.2
  • 21
    • 85039525817 scopus 로고    scopus 로고
    • note
    • A detailed description of the syntheses can be found in Supporting Information. See also Supporting Information of ref 3.
  • 22
    • 85039520363 scopus 로고    scopus 로고
    • note
    • The relative stereochemistry of the syn-27 and anti-27 precursors was assigned on the basis of the relative stereochemistry of the corresponding cyclized products 38 and 40 (these were assigned by analysis of the coupling constant between the secondary benzylic hydrogens and the neighboring tertiary silyl ether hydrogen).
  • 23
  • 31
    • 0037419357 scopus 로고    scopus 로고
    • For a discussion of the influence of ortho substituents in radical mediated cyclizations, see: Curran, D. P.; Fairweather, N. J. Org. Chem. 2003, 68, 2972-2974.
    • (2003) J. Org. Chem. , vol.68 , pp. 2972-2974
    • Curran, D.P.1    Fairweather, N.2
  • 32
    • 85039520756 scopus 로고    scopus 로고
    • note
    • Configurations were tentatively assigned on the basis of the observation of a trans-diaxial coupling constant (11 Hz) between the proton adjacent to the OTBS group and one of the benzylic methylene protons in anti-27. Both modeling and the crystal structure of 54 indicated a dihedral angle of close to 180° in this isomer.
  • 34
    • 85039526564 scopus 로고    scopus 로고
    • note
    • Experiment performed in the cyclized products 48 and 50.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.