A highly efficient and convergent reaction for the synthesis of bridgehead enone-containing polycyclic ring systems

Angewandte Chemie - International Edition

Volumn 39, Issue 15, 2000, Pages 2714-2715

  Sheehan, Scott M ^a   Lalic, Gojko ^a   Chen, Jason S ^a   Shair, Matthew D ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Cyclizations; Cycloadditions; Domino reactions; Grignard reactions; Polycycles

Indexed keywords

POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034604574     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2714::AID-ANIE2714>3.0.CO;2-1     Document Type: Article

References (26)

1. Naturally occurring molecules that contain this ring system include: a) CP-263,114 and CP-225,917: T. T. Dabrah, H. L. Harwood, L. G. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, Antibiotics 1997, 50, 1; T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; b) taxol and taxus terpenes: M. C. Wani, M. E. Taylor, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325; c) welwitindolinone: K. Stratmann, D. L. Burgoyne, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1994, 59, 7219; K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935.
2. Naturally occurring molecules that contain this ring system include: a) CP-263,114 and CP-225,917: T. T. Dabrah, H. L. Harwood, L. G. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, Antibiotics 1997, 50, 1; T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; b) taxol and taxus terpenes: M. C. Wani, M. E. Taylor, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325; c) welwitindolinone: K. Stratmann, D. L. Burgoyne, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1994, 59, 7219; K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935.
3. Naturally occurring molecules that contain this ring system include: a) CP-263,114 and CP-225,917: T. T. Dabrah, H. L. Harwood, L. G. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, Antibiotics 1997, 50, 1; T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; b) taxol and taxus terpenes: M. C. Wani, M. E. Taylor, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325; c) welwitindolinone: K. Stratmann, D. L. Burgoyne, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1994, 59, 7219; K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935.
4. Naturally occurring molecules that contain this ring system include: a) CP-263,114 and CP-225,917: T. T. Dabrah, H. L. Harwood, L. G. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, Antibiotics 1997, 50, 1; T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; b) taxol and taxus terpenes: M. C. Wani, M. E. Taylor, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325; c) welwitindolinone: K. Stratmann, D. L. Burgoyne, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1994, 59, 7219; K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935.
5. Naturally occurring molecules that contain this ring system include: a) CP-263,114 and CP-225,917: T. T. Dabrah, H. L. Harwood, L. G. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, Antibiotics 1997, 50, 1; T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594; b) taxol and taxus terpenes: M. C. Wani, M. E. Taylor, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325; c) welwitindolinone: K. Stratmann, D. L. Burgoyne, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1994, 59, 7219; K. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935.
6. For a review of the intramolecular Diels-Alder reaction, see W. R. Roush in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 513.
7. a) K. J. Shea, P. D. Davis, Angew. Chem. 1983, 95, 422; Angew. Chem. Int. Ed. Engl. 1983, 223, 419;
8. a) K. J. Shea, P. D. Davis, Angew. Chem. 1983, 95, 422; Angew. Chem. Int. Ed. Engl. 1983, 223, 419;
9. b) K. J. Shea, J. W. Gilman, C. D. Haffner, T. K. Dougherty, J. Am. Chem. Soc. 1986, 108, 4953;
10. c) K. J. Shea, C. D. Haffner, Tetrahedron Lett. 1988, 29, 1367;
11. d) K. J. Shea, S. T. Sakata, Tetrahedron Lett. 1992, 33, 4264;
12. e) R. W. Jackson, R. G. Higby, J. W. Gilman, K. J. Shea, Tetrahedron 1992, 48, 7013;
13. f) R. W. Jackson, K. J. Shea, Tetrahedron Lett. 1994, 35, 1317;
14. g) K. J. Shea, C. D. Haffner, Tetrahedron Lett. 1998, 29, 1367.
15. a) M. G. Moloney, J. T. Pinhey, M. J. Stoermer, J. Chem. Soc. Perkin Trans. 1 1990, 2645;
16. b) C. J. Parkinson, J. T. Pinhey, M. J. Stoermer, J. Chem. Soc.: Perkin Trans. 1 1992, 1911.
17. D. A. Evans, A. M. Golob, J. Am. Chem. Soc. 1975, 97, 4765.
18. C. Chen, M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784.
19. Each of the new compounds reported in this article was fully characterized, see the Supporting Information for details.
20. For the synthesis of taxanes with aryl C-rings, see a) K. C. Nicolaou, W. M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 15; Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references therein; b) W. B. Young, J. J. Masters, S. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5228; c) K. C. Nicolaou, C. G. Claiborne, K. Paulvannan, M. A. D. Postema, R. K. Guy, Chem. Eur. J. 1997, 3, 399; d) A. G. Fallis, Acc. Chem Res. 1999, 32, 464; e) see also ref. [3].
21. For the synthesis of taxanes with aryl C-rings, see a) K. C. Nicolaou, W. M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 15; Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references therein; b) W. B. Young, J. J. Masters, S. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5228; c) K. C. Nicolaou, C. G. Claiborne, K. Paulvannan, M. A. D. Postema, R. K. Guy, Chem. Eur. J. 1997, 3, 399; d) A. G. Fallis, Acc. Chem Res. 1999, 32, 464; e) see also ref. [3].
22. For the synthesis of taxanes with aryl C-rings, see a) K. C. Nicolaou, W. M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 15; Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references therein; b) W. B. Young, J. J. Masters, S. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5228; c) K. C. Nicolaou, C. G. Claiborne, K. Paulvannan, M. A. D. Postema, R. K. Guy, Chem. Eur. J. 1997, 3, 399; d) A. G. Fallis, Acc. Chem Res. 1999, 32, 464; e) see also ref. [3].
23. For the synthesis of taxanes with aryl C-rings, see a) K. C. Nicolaou, W. M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 15; Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references therein; b) W. B. Young, J. J. Masters, S. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5228; c) K. C. Nicolaou, C. G. Claiborne, K. Paulvannan, M. A. D. Postema, R. K. Guy, Chem. Eur. J. 1997, 3, 399; d) A. G. Fallis, Acc. Chem Res. 1999, 32, 464; e) see also ref. [3].
24. For the synthesis of taxanes with aryl C-rings, see a) K. C. Nicolaou, W. M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 15; Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references therein; b) W. B. Young, J. J. Masters, S. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5228; c) K. C. Nicolaou, C. G. Claiborne, K. Paulvannan, M. A. D. Postema, R. K. Guy, Chem. Eur. J. 1997, 3, 399; d) A. G. Fallis, Acc. Chem Res. 1999, 32, 464; e) see also ref. [3].
25. For the synthesis of taxanes with aryl C-rings, see a) K. C. Nicolaou, W. M. Dai, R. K. Guy, Angew. Chem. 1994, 106, 15; Angew. Chem. Int. Ed. Engl. 1994, 33, 15, and references therein; b) W. B. Young, J. J. Masters, S. Danishefsky, J. Am. Chem. Soc. 1995, 117, 5228; c) K. C. Nicolaou, C. G. Claiborne, K. Paulvannan, M. A. D. Postema, R. K. Guy, Chem. Eur. J. 1997, 3, 399; d) A. G. Fallis, Acc. Chem Res. 1999, 32, 464; e) see also ref. [3].
26. For an article discussing diversity-oriented synthesis, see S. L. Schreiber, Science 2000, 287, 1964.