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Volumn 52, Issue 4, 1987, Pages 569-580

Two Approaches to Angularly Fused Triquinanes via Intramolecular Pauson-Khand Cyclization

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EID: 33845281184     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00380a017     Document Type: Article
Times cited : (53)

References (35)
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    • General references for the Pauson-Khand reaction
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    • General references for the Pauson-Khand reaction: (a) Khand, U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chen Soc., Perkin Trans. 1 1973, 977. (b) Pauson, P. L.; Khand, I. U. Anr N. Y. Acad. Sci. 1977, 295, 2. (c) Pauson, P. L. Tetrahedron 1985, 4, 5855.
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    • (b) Exon, C.; Magnus, P. J. Am. Chem. Soc. 1983,105, 2477. (c) Magnus P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851, (d) Magnus, P Exon, C.; Albaugh-Robertson, P. Tetrahedron 1985, 41, 5861. (e) Huf D. H. J. Am. Chem. Soc. 1986. 108, 3835
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    • (b) Billington, D. C.; Willison, D. Tetrahedron Lett. 1984, 25, 4041. (c) Simonian, S. O.; Smit, W. A.; Gybin, A. S.; Shashkov, A. S.; Mikaelian, G. S.; Tarasov, V. A.; Ibragimov, 1.1.; Caple, R.; Froen, D. E. Tetrahedron Lett. 1986, 27,1245; (d) Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128.
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    • The intermolcular Pauson-Khand reaction has also been used in syntheses of several of these systems
    • (b) Daalman, L.; Newton, R. F.; Pauson, P. L.; Wadsworth, A. J. Chem. Res. Miniprint 1984, 3150. (c) Billington, D. C. Tetrahedron Lett. 1983, 24, 2905.
    • The intermolcular Pauson-Khand reaction has also been used in syntheses of several of these systems: (a) Newton, R. F.; Pauson, P. L.; Taylor, R. G. J. Chem. Res. Miniprint 1980, 3501. (b) Daalman, L.; Newton, R. F.; Pauson, P. L.; Wadsworth, A. J. Chem. Res. Miniprint 1984, 3150. (c) Billington, D. C. Tetrahedron Lett. 1983, 24, 2905.
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    • Ketone 2 has been reported previously
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    • Compare experiment 5 in
    • Compare experiment 5 in Greene, A. E. J. Am. Chem. Soc. 1980, 102, 5337.
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    • Syntheses
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    • Syntheses: Paquette, L.; Han, Y. K. J. Org. Chem. 1979,44,4014. Oppolzer, W.; Battig, K.; Hudlicky, T. Helv. Chim. Acta 1979, 62, 1493. Pirrung, M. C. J. Am. Chem. Soc. 1979, 101, 7130. Dauben, W. G.; Walker, D. M. J. Org. Chem. 1981, 46, 1103. Wender, P. A.; Dreyer, G. B. Tetrahedron 1981, 37, 4445. Tobe, Y.; Yamashita, T.; Kakaiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898.
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    • Syntheses
    • (b) Paquette, L. A.; Annis, G. D. J. Am. Chem. Soc. 1982,104,4504. (c) Piers, E.; Karunaratne, V. J. Chem. Soc., Chem. Commun. 1984, 959. (d) Pattenden, G.; Teague, S. J. Tetrahedron Lett. 1984, 3021. (e) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800. See also ref 2e for a synthesis of (+)-17 using the intramolecular Pauson-Khand cyclization of an acyclic enyne.
    • Syntheses: (a) Ohfune, Y.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1976, 2869. (b) Paquette, L. A.; Annis, G. D. J. Am. Chem. Soc. 1982,104,4504. (c) Piers, E.; Karunaratne, V. J. Chem. Soc., Chem. Commun. 1984, 959. (d) Pattenden, G.; Teague, S. J. Tetrahedron Lett. 1984, 3021. (e) Crimmins, M. T.; DeLoach, J. A. J. Am. Chem. Soc. 1986, 108, 800. See also ref 2e for a synthesis of (+)-17 using the intramolecular Pauson-Khand cyclization of an acyclic enyne.
    • (1976) Tetrahedron Lett. , pp. 2869
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    • Syntheses
    • Tsunoda, T.; Kodama, M.; Ito, S. Tetrahedron Lett. 1983, 24, 83. Sternbach, D. D.; Hughes, J. W.; Burdi, D. F.; Banks, B. A. J. Am. Chem. Soc. 1985,107, 2149. Wender, P. A. Tetrahedron Lett. 1985, 26, 2625. Crimmins, M. T.; Mascarella, S. W. J. Am. Chem. Soc. 1986, 108, 3435.
    • Syntheses: Leone-Bay, A.; Paquette, L. A. J. Org. Chem. 1983, 47, 4173. Tsunoda, T.; Kodama, M.; Ito, S. Tetrahedron Lett. 1983, 24, 83. Sternbach, D. D.; Hughes, J. W.; Burdi, D. F.; Banks, B. A. J. Am. Chem. Soc. 1985,107, 2149. Wender, P. A. Tetrahedron Lett. 1985, 26, 2625. Crimmins, M. T.; Mascarella, S. W. J. Am. Chem. Soc. 1986, 108, 3435.
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