Synthesis of the Bicyclic Core of CP-225,917 and CP-263,114 by an Intramolecular Diels-Alder Reaction

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 11, 1997, Pages 1194-1196

  Nicolaou, K C ^a,b   Härter, Michael W ^a   Boulton, Lee ^a   Jandeleit, Bernd ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Bicycles; Diels Alder reactions; Natural products; Synthetic methods

Indexed keywords

EID: 0030749472     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199711941     Document Type: Article

References (16)

1. T. T. Dabrah, H. J. Harwood Jr., L. H. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, J. Antibiot. 1997, 50, 1.
2. T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594. We thank Dr. T. Kaneko for a preprint of this paper.
3. G. Popják, W. S. Agnew, Mol. Cell. Biochem. 1979, 27, 97.
4. S. Clarke, Annu. Rev. Biochem. 1992, 61, 355.
5. J. L. Goldstein, M. S. Brown, Nature 1990, 343, 425.
6. J. E. Buss, J. C. Marsters, Chem. Biol. 1995, 2, 787.
7. Reviews on intramolecular Diels-Alder reactions: a) E. Ciganek, Org. Synth. 1984, 32, 1; b) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513; c) G. Helmchen in Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E21c, Thieme, Stuttgart, 1995, p. 2872; construction of the bicyclo[4.3.1]dec-1(9)-ene system by an intramolecular Diels-Alder reaction: d) K. J. Shea, S. Wise, J. Am. Chem. Soc. 1978, 100, 6519; e) Tetrahedron Lett. 1979, 1011; f) S. L. Gwaltney, S. T. Sakata, K. J. Shea, ibid. 1995, 7177.
8. Reviews on intramolecular Diels-Alder reactions: a) E. Ciganek, Org. Synth. 1984, 32, 1; b) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513; c) G. Helmchen in Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E21c, Thieme, Stuttgart, 1995, p. 2872; construction of the bicyclo[4.3.1]dec-1(9)-ene system by an intramolecular Diels-Alder reaction: d) K. J. Shea, S. Wise, J. Am. Chem. Soc. 1978, 100, 6519; e) Tetrahedron Lett. 1979, 1011; f) S. L. Gwaltney, S. T. Sakata, K. J. Shea, ibid. 1995, 7177.
9. Reviews on intramolecular Diels-Alder reactions: a) E. Ciganek, Org. Synth. 1984, 32, 1; b) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513; c) G. Helmchen in Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E21c, Thieme, Stuttgart, 1995, p. 2872; construction of the bicyclo[4.3.1]dec-1(9)-ene system by an intramolecular Diels-Alder reaction: d) K. J. Shea, S. Wise, J. Am. Chem. Soc. 1978, 100, 6519; e) Tetrahedron Lett. 1979, 1011; f) S. L. Gwaltney, S. T. Sakata, K. J. Shea, ibid. 1995, 7177.
10. Reviews on intramolecular Diels-Alder reactions: a) E. Ciganek, Org. Synth. 1984, 32, 1; b) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513; c) G. Helmchen in Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E21c, Thieme, Stuttgart, 1995, p. 2872; construction of the bicyclo[4.3.1]dec-1(9)-ene system by an intramolecular Diels-Alder reaction: d) K. J. Shea, S. Wise, J. Am. Chem. Soc. 1978, 100, 6519; e) Tetrahedron Lett. 1979, 1011; f) S. L. Gwaltney, S. T. Sakata, K. J. Shea, ibid. 1995, 7177.
11. Reviews on intramolecular Diels-Alder reactions: a) E. Ciganek, Org. Synth. 1984, 32, 1; b) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513; c) G. Helmchen in Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E21c, Thieme, Stuttgart, 1995, p. 2872; construction of the bicyclo[4.3.1]dec-1(9)-ene system by an intramolecular Diels-Alder reaction: d) K. J. Shea, S. Wise, J. Am. Chem. Soc. 1978, 100, 6519; e) Tetrahedron Lett. 1979, 1011; f) S. L. Gwaltney, S. T. Sakata, K. J. Shea, ibid. 1995, 7177.
12. Reviews on intramolecular Diels-Alder reactions: a) E. Ciganek, Org. Synth. 1984, 32, 1; b) W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513; c) G. Helmchen in Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E21c, Thieme, Stuttgart, 1995, p. 2872; construction of the bicyclo[4.3.1]dec-1(9)-ene system by an intramolecular Diels-Alder reaction: d) K. J. Shea, S. Wise, J. Am. Chem. Soc. 1978, 100, 6519; e) Tetrahedron Lett. 1979, 1011; f) S. L. Gwaltney, S. T. Sakata, K. J. Shea, ibid. 1995, 7177.
13. U. Hertenstein, S. Hünig, M. Öller, Chem. Ber. 1980, 113, 3783.
14. G. Wittig, H. Reiff, Angew. Chem. 1968, 80, 8; Angew. Chem. Int. Ed. Engl. 1968, 7, 7.
15. G. Wittig, H. Reiff, Angew. Chem. 1968, 80, 8; Angew. Chem. Int. Ed. Engl. 1968, 7, 7.
16. All new compounds exhibited satisfactory spectral and/or exact mass data. Yields refer to chromatographically and spectroscopically homogeneous materials.