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Volumn 9, Issue 6, 2007, Pages 1138-1143

Solid phase synthesis of highly substituted tetrahydropyrans by tandem ene-reaction/intramolecular sakurai cyclization

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; PYRAN DERIVATIVE;

EID: 36649003283     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc7001099     Document Type: Article
Times cited : (11)

References (39)
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    • and refs. therein
    • Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348-4378, and refs. therein.
    • (2005) Chem. Rev , vol.105 , pp. 4348-4378
    • Kang, E.J.1    Lee, E.2
  • 15
    • 4544365737 scopus 로고    scopus 로고
    • For previous reports on such syntheses from our laboratory see
    • (a) For previous reports on such syntheses from our laboratory see: Spiroacetals Barun, O.; Sommer, S.; Waldmann, H. Angew. Chem. Int. Ed. 2004, 43, 3195-3199.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3195-3199
    • Spiroacetals Barun, O.1    Sommer, S.2    Waldmann, H.3
  • 17
    • 27844607742 scopus 로고    scopus 로고
    • Barun, O.; Kumar, K.; Sommer, S.; Langerak, A.; Mayer, T. U.; Müller, O.; Waldmann, H. Eur. J. Org. Chem. 2005, 22, 4773-4788 α,ß-Unsaturated lactones.
    • (c) Barun, O.; Kumar, K.; Sommer, S.; Langerak, A.; Mayer, T. U.; Müller, O.; Waldmann, H. Eur. J. Org. Chem. 2005, 22, 4773-4788 α,ß-Unsaturated lactones.
  • 21
    • 33748268305 scopus 로고    scopus 로고
    • Tetrahydropyrans:(g) Sanz, M. A.; Voigt, T.; Waldmann, H. Adv. Synth. Catal. 2006, 348, 1511-1515.
    • Tetrahydropyrans:(g) Sanz, M. A.; Voigt, T.; Waldmann, H. Adv. Synth. Catal. 2006, 348, 1511-1515.
  • 26
    • 34548575524 scopus 로고    scopus 로고
    • Indoloquinolizidines see also ref. 10 and Corrêa, I. R., Jr.; Noeren-Mueller, A.; Ambrosi, H. D.; Jakupovic, S.; Saxena, K.; Schwalbe, H.; Prinz, H.; Kaiser, M.; Waldman, H. Chem. Asian J. 2007, 2, 1109-1126. Decalins:.
    • Indoloquinolizidines see also ref. 10 and Corrêa, I. R., Jr.; Noeren-Mueller, A.; Ambrosi, H. D.; Jakupovic, S.; Saxena, K.; Schwalbe, H.; Prinz, H.; Kaiser, M.; Waldman, H. Chem. Asian J. 2007, 2, 1109-1126. Decalins:.
  • 30
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    • Stahl, P.; Kissau, L.; Matzischek, R.; Giannis, A.; Waldmann, H. Angew. Chem. Int. Ed. 2002, 41, 1174-1178, see also ref. 8.
    • (o) Stahl, P.; Kissau, L.; Matzischek, R.; Giannis, A.; Waldmann, H. Angew. Chem. Int. Ed. 2002, 41, 1174-1178, see also ref. 8.
  • 35
    • 33846140465 scopus 로고    scopus 로고
    • van Innis, L.; Plancher, J.; Marko, M.; I. E. Org. Lett. 2006, 8, 6111-6114.
    • (e) van Innis, L.; Plancher, J.; Marko, M.; I. E. Org. Lett. 2006, 8, 6111-6114.
  • 37
    • 36649019467 scopus 로고    scopus 로고
    • The cyclohexyl substituent at C2 and the hydroxyl substituent at C3 are in equatorial position as shown by the coupling constant between H2 and H3, 3J2,3, 9.4 Hz) which is typical for an axial/axial orientation of the corresponding protons at C2 and C3 (typically 3 Jax,ax, 8-10 Hz, The proton H6 is coupled to one of the protons at C5 with a small coupling constant (3J6,5, 2.1 Hz, which can be either an axial/ equatorial or an equatorial/equatorial interaction, and to the other with a large coupling constant (3J6,5′, 12.5 Hz) typical for an axial/axial interaction whereas typically 3Jax/eq, 3Jeq/eq, 2-3 Hz, This large coupling constant shows that H5′ is HRe, trans to H6, and that H6 is in axial position. Such a finding is well-known for tetrahydropyrans and glucosides and has previo
    • Re, trans to H6, and that H6 is in axial position. Such a finding is well-known for tetrahydropyrans and glucosides and has previously been employed to correctly assign the relative stereochemistry of 4-exo-methylene tetrahydropyrans present for example in Zampanolide (see J-I Tanaka, T. Higa, Tetrahedron Lett. 1996, 37, 5535-5538) and in Dactylolide (see Cutignano, A.; Bruno, I.; Bifulco, G.; Casapullo, A.; Debitus, C.; Gomez-Paloma, L.; Riccio, R. Eur. J. Org. Chem., 2001, 775-778).
  • 39
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    • An ene-reaction on solid support has been reported as part of a domino-reaction Tietze, L. F, Steinmetz, A. Angew. Chem 1996, 108, 682-683
    • An ene-reaction on solid support has been reported as part of a domino-reaction Tietze, L. F.; Steinmetz, A. Angew. Chem 1996, 108, 682-683.


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