Enantioselective Diels-Alder Approach to Angucyclinones from (S)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone and Substituted Racemic Vinylcyclohexenes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 15, 1997, Pages 1621-1623

  Carreño, M Carmen ^a   Urbano, Antonio ^a   Fischer, Jean ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Angucyclinones; Antibiotics; Asymmetric synthesis; Cycloadditions; Quinones

Indexed keywords

EID: 0030763184     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199716211     Document Type: Article

References (40)

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6. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
7. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
8. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
9. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
10. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
11. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
12. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
13. Recent work: a) K. Kim, J. Reibenspies, G. Sulikowski, J. Org. Chem. 1992, 57, 5557-5559; b) K. Krohn, F. Ballwanz, W. Baltus, Liebigs Ann. Chem. 1993, 911-913; c) K. Krohn, K. Khanbabaee, ibid. 1994, 1109-1112; d) F. L. Andrews, D. S. Larsen, Tetrahedron Lett. 1994, 35, 8693-8696; e) K. Krohn, W. Dröge, F. Hintze, Ann. Quim. 1995, 91, 388-393; f) V. A. Boyd, J. Reibenspies, G. A. Sulikowski, Tetrahedron Lett. 1995, 36, 4001-4004; g) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866-6871; h) D. S. Larsen, M. D. O'Shea, ibid. 1996, 61, 5681-5683.
14. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
15. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
16. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
17. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
18. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
19. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
20. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
21. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
22. Recent work: a) D. S. Larsen, M. D. O'Shea, Tetrahedron Lett. 1993, 34, 1373-1376; b) K. Krohn, K. Khanbabaee, Angew. Chem. 1994, 106, 100-102; Angew. Chem. Int. Ed. Engl. 1994, 33, 99-100; c) D. S. Larsen, M. D. O'Shea, J. Chem. Soc. Perkin Trans. 1 1995, 1019-1028; d) K. Kim, G. A. Sulikowski, Angew. Chem. 1995, 107, 2587-2589; Angew. Chem. Int. Ed. Engl. 1995, 34, 2396-2398; e) V. A. Boyd, G. A. Sulikowski, J. Am. Chem. Soc. 1995, 117, 8472-8473; f) D. S. Larsen, M. D. O'Shea, S. Brooker, Chem. Commun. 1996, 203-204; g) G. Matsuo, Y. Miki, M. Nakata, S. Matsumura, K. Toshima, ibid. 1996, 225-226.
23. Overview of our work: a) M. C. Carreño, Chem. Rev. 1995, 95, 1717-1760; recent work: b) M. C. Carreño, J. L. García Ruano, M. A. Toledo, A. Urbano, V. Stefani, C. Z. Remor, J. Fischer, J. Org. Chem. 1996, 61, 503-509; M. C. Carreño, J. L. García Ruano, A. Urbano, M. A. Hoyos, ibid. 1996, 61, 2980-2985; d) M. C. Carreño, J. L. García Ruano, A. Urbano, M. I. López-Solera, ibid. 1997, 62, 976-981.
24. Overview of our work: a) M. C. Carreño, Chem. Rev. 1995, 95, 1717-1760; recent work: b) M. C. Carreño, J. L. García Ruano, M. A. Toledo, A. Urbano, V. Stefani, C. Z. Remor, J. Fischer, J. Org. Chem. 1996, 61, 503-509; M. C. Carreño, J. L. García Ruano, A. Urbano, M. A. Hoyos, ibid. 1996, 61, 2980-2985; d) M. C. Carreño, J. L. García Ruano, A. Urbano, M. I. López-Solera, ibid. 1997, 62, 976-981.
25. Overview of our work: a) M. C. Carreño, Chem. Rev. 1995, 95, 1717-1760; recent work: b) M. C. Carreño, J. L. García Ruano, M. A. Toledo, A. Urbano, V. Stefani, C. Z. Remor, J. Fischer, J. Org. Chem. 1996, 61, 503-509; c) M. C. Carreño, J. L. García Ruano, A. Urbano, M. A. Hoyos, ibid. 1996, 61, 2980-2985; d) M. C. Carreño, J. L. García Ruano, A. Urbano, M. I. López-Solera, ibid. 1997, 62, 976-981.
26. Overview of our work: a) M. C. Carreño, Chem. Rev. 1995, 95, 1717-1760; recent work: b) M. C. Carreño, J. L. García Ruano, M. A. Toledo, A. Urbano, V. Stefani, C. Z. Remor, J. Fischer, J. Org. Chem. 1996, 61, 503-509; M. C. Carreño, J. L. García Ruano, A. Urbano, M. A. Hoyos, ibid. 1996, 61, 2980-2985; d) M. C. Carreño, J. L. García Ruano, A. Urbano, M. I. López-Solera, ibid. 1997, 62, 976-981.
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35. The relative configuration was established by comparison with a similar intermediate prepared by Sulikowski [5d] in the total synthesis of SF 2315A.
36. When the cycloaddition was carried out in water the reaction was faster (completed in 12 h at room temperature) but with a lower enantiomeric excess (20%).
37. 3] for 7b and 7d. The required racemic compounds were obtained from racemic quinone 1 [8].
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39. The absolute structure was determined by comparing refinements of both configurations, and confirmed by refining Flack's x parameter (G. Bernardinelli, H. D. Flack, Acta Crystallogr. Sect. A 1987, 43, 75-78). Crystallographic data (excluding structure factors) for (+)-5d have been deposited with the Cambridge Crystallographic Data Centre as suplementary publication no. CCDC-100127. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
40. These results contradict those reported by Sulikowski et al. [4g], who described no reaction for a similar system with DBU in benzene at 0°C.