PtCl2-catalyzed transannular cycloisomerization of 1,5-enynes: A new efficient regio- and stereocontrolled access to tricyclic derivatives

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3771-3774

  Blaszykowski, Christophe ^a   Harrak, Youssef ^a   Gonçalves, Maria Helena ^a   Cloarec, Jean Manuel ^a   Dhimane, Anne Lise ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PLATINUM DERIVATIVE; TRICYCLIC AROMATIC COMPOUND;

ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 7044286289     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048463n     Document Type: Article

References (44)

1. For a review, see: Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260. See also: Caussanel, F.; Deslongchamps, P.; Dory, Y. L. Org. Lett. 2003, 5, 4799-4802.
2. For a review, see: Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260. See also: Caussanel, F.; Deslongchamps, P.; Dory, Y. L. Org. Lett. 2003, 5, 4799-4802.
3. Handa, S.; Pattenden, G. Contemp. Org. Synth. 1997, 4, 196-215. See also: Dhimane, A. L.; Fensterbank, L.; Malacria, M. In Radicals in Organic Synthesis; Renaud, P., Sibi M. P., Eds.; Wiley-VCH: Weiheim, 2001; Vol. 2, pp 350-382.
4. Handa, S.; Pattenden, G. Contemp. Org. Synth. 1997, 4, 196-215. See also: Dhimane, A. L.; Fensterbank, L.; Malacria, M. In Radicals in Organic Synthesis; Renaud, P., Sibi M. P., Eds.; Wiley-VCH: Weiheim, 2001; Vol. 2, pp 350-382.
5. Rychlet Elliott, M.; Dhimane, A. L.; Malacria, M. J. Am. Chem. Soc. 1997, 119, 3427-3428.
6. Dhimane, A. L.; Aïssa, C.; Malacria M. Angew. Chem., Int. Ed. 2002, 41, 3284-3287.
7. (a) Diyne transannular reactivity with rhodium: King, R. B.; Ackermann M. N. J. Organomet. Chem. 1974, 67, 431-441. (b) With iron: King, R. B.; Haiduc, I.; Eavenson, C. W. J. Am. Chem. Soc. 1973, 95, 2508-2516. (c) With cobalt: King, R. B.; Efraty, A. J. Am. Chem. Soc. 1972, 94, 3021-3025. (d) For a recent contribution: Pla-Quintana, A.; Roglans, A.; Torrent, A.; Moreno-Mañas, M.; Benet-Buchholz, J. Organometallics 2004, 23, 2762-2767 and references therein.
8. (a) Diyne transannular reactivity with rhodium: King, R. B.; Ackermann M. N. J. Organomet. Chem. 1974, 67, 431-441. (b) With iron: King, R. B.; Haiduc, I.; Eavenson, C. W. J. Am. Chem. Soc. 1973, 95, 2508-2516. (c) With cobalt: King, R. B.; Efraty, A. J. Am. Chem. Soc. 1972, 94, 3021-3025. (d) For a recent contribution: Pla-Quintana, A.; Roglans, A.; Torrent, A.; Moreno-Mañas, M.; Benet-Buchholz, J. Organometallics 2004, 23, 2762-2767 and references therein.
9. (a) Diyne transannular reactivity with rhodium: King, R. B.; Ackermann M. N. J. Organomet. Chem. 1974, 67, 431-441. (b) With iron: King, R. B.; Haiduc, I.; Eavenson, C. W. J. Am. Chem. Soc. 1973, 95, 2508-2516. (c) With cobalt: King, R. B.; Efraty, A. J. Am. Chem. Soc. 1972, 94, 3021-3025. (d) For a recent contribution: Pla-Quintana, A.; Roglans, A.; Torrent, A.; Moreno-Mañas, M.; Benet-Buchholz, J. Organometallics 2004, 23, 2762-2767 and references therein.
10. (a) Diyne transannular reactivity with rhodium: King, R. B.; Ackermann M. N. J. Organomet. Chem. 1974, 67, 431-441. (b) With iron: King, R. B.; Haiduc, I.; Eavenson, C. W. J. Am. Chem. Soc. 1973, 95, 2508-2516. (c) With cobalt: King, R. B.; Efraty, A. J. Am. Chem. Soc. 1972, 94, 3021-3025. (d) For a recent contribution: Pla-Quintana, A.; Roglans, A.; Torrent, A.; Moreno-Mañas, M.; Benet-Buchholz, J. Organometallics 2004, 23, 2762-2767 and references therein.
11. (a) Transannular oxypalladation: Sasaki, T.; Kanematsu, K.; Kondo A. J. Chem. Soc., Perkin Trans. 1 1976, 2516-2520. (b) Transannular [3 + 2] TMM-like cycloaddition: Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081-3088. (c) Transannular carbopalladation: Ohe, K.; Miki, K.; Yanagi, S.-I.; Tanaka, T.; Sawada, S.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 3627-3634.
12. (a) Transannular oxypalladation: Sasaki, T.; Kanematsu, K.; Kondo A. J. Chem. Soc., Perkin Trans. 1 1976, 2516-2520. (b) Transannular [3 + 2] TMM-like cycloaddition: Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081-3088. (c) Transannular carbopalladation: Ohe, K.; Miki, K.; Yanagi, S.-I.; Tanaka, T.; Sawada, S.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 3627-3634.
13. (a) Transannular oxypalladation: Sasaki, T.; Kanematsu, K.; Kondo A. J. Chem. Soc., Perkin Trans. 1 1976, 2516-2520. (b) Transannular [3 + 2] TMM-like cycloaddition: Yamago, S.; Nakamura, E. Tetrahedron 1989, 45, 3081-3088. (c) Transannular carbopalladation: Ohe, K.; Miki, K.; Yanagi, S.-I.; Tanaka, T.; Sawada, S.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 3627-3634.
14. For reviews, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (b) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397. (c) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
15. For reviews, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (b) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397. (c) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
16. For reviews, see: (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (b) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts-Org. Chem. 2003, 16, 397. (c) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
17. For recent publications, see: (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635. (b) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105. (c) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (f) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
18. For recent publications, see: (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635. (b) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105. (c) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (f) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
19. For recent publications, see: (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635. (b) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105. (c) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (f) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
20. For recent publications, see: (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635. (b) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105. (c) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (f) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
21. For recent publications, see: (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635. (b) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105. (c) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (f) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
22. For recent publications, see: (a) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635. (b) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105. (c) Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810. (d) Charruault, L.; Michelet, V.; Taras, R.; Gladiali, S.; Genêt, J.-P. Chem. Commun. 2004, 850-851. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869. (f) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
23. Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409.
24. Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509-1511.
25. Mainetti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M. Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132-2135.
26. (a) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.: Mouriès, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656-8657.
27. For similar findings, see: (b) Mamane, V.; Gress, T.; Krause, H.; Fürstner A. J. Am. Chem. Soc. 2004, 126, 8654-8655.
28. (a) Takai, K.; Kuroda, T.; Nakatsukasa, S.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 5585-5588.
29. (b) Rychlet Elliott, M.; Dhimane, A. L.; Hamon, L.; Malacria, M. Eur. J. Org. Chem. 2000, 155-163.
30. For other access to these intriguing skeletons, see: (a) Hannah, D. J.; Smith, R. A. J.; Teoh, I.; Weavers, R. T. Aust. J. Chem. 1981, 34, 181-188. (b) Marshall, J. A.; Peterson, J. C.; Lebioda, L. J. Am. Chem. Soc. 1984, 106, 6006-6015. (c) Ricci, A.; Fasani, E.; Mella, M.; Albini, A. J. Org. Chem. 2003, 68, 4361-4366.
31. For other access to these intriguing skeletons, see: (a) Hannah, D. J.; Smith, R. A. J.; Teoh, I.; Weavers, R. T. Aust. J. Chem. 1981, 34, 181-188. (b) Marshall, J. A.; Peterson, J. C.; Lebioda, L. J. Am. Chem. Soc. 1984, 106, 6006-6015. (c) Ricci, A.; Fasani, E.; Mella, M.; Albini, A. J. Org. Chem. 2003, 68, 4361-4366.
32. For other access to these intriguing skeletons, see: (a) Hannah, D. J.; Smith, R. A. J.; Teoh, I.; Weavers, R. T. Aust. J. Chem. 1981, 34, 181-188. (b) Marshall, J. A.; Peterson, J. C.; Lebioda, L. J. Am. Chem. Soc. 1984, 106, 6006-6015. (c) Ricci, A.; Fasani, E.; Mella, M.; Albini, A. J. Org. Chem. 2003, 68, 4361-4366.
33. Warmers, U.; König, W. A. Phytochemistry 1999, 52, 1519-1524.
34. Hayashi, K.-I.; Asano, K.-I.; Tanaka, M.; Takaoka, D.; Nozaki, H. Phytochemistry 1998, 48, 461-466.
35. Shi, J.-G.; Shi, Y.-P.; Jia, Z.-J. Phytochemistry 1997, 45, 343-347.
36. Endo, Y.; Ohta, T.; Nozoe, S. Tetrahedron Lett. 1991, 32, 5555-5558.
37. Aïssa, C.; Dhimane, A.-L.; Malacria, M. Synlett 2000, 1585-1588.
38. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186.
39. Stereochemical assignments were performed by using NOE studies. See the Supporting Information.
40. (a) For pioneering findings, see: Rautenstrauch, V. J. Org. Chem. 1984, 49, 950-952. (b) For an intermolecular version, see: Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505-8513.
41. (a) For pioneering findings, see: Rautenstrauch, V. J. Org. Chem. 1984, 49, 950-952. (b) For an intermolecular version, see: Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505-8513.
42. Whether involving carbenoid or carbocationic intermediates, similar 1,2-hydrogen transfers have been observed by Echavarren, Fürstner, and us on several precursors; see refs 8e,f and 12a,b.
43. CCDC 243389 contains the supplementary crystallographic data for 18 that can be obtained, free of charge, from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/conts/retrieving.html.
44. For related formation of allenes, see refs 9 and 23b and references therein.