Studies on oxidopyrylium [5 + 2] cycloadditions: Toward a general synthetic route to the C12-hydroxy daphnetoxins

Organic Letters

Volumn 8, Issue 23, 2006, Pages 5373-5376

  Wender, Paul A ^a,b   Bi, F Christopher ^a   Buschmann, Nicole ^a   Gosselin, Francis ^a   Kan, Cindy ^a   Kee, Jung Min ^a   Ohmura, Hirofumi ^a  

^a STANFORD UNIVERSITY   (United States)

^b STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRIDGED COMPOUND; DITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

BRIDGED COMPOUNDS; CYCLIZATION; DITERPENES; MOLECULAR STRUCTURE;

EID: 33845236874     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062234e     Document Type: Article

References (42)

1. For reviews on daphnane diterpenes, see: (a) Kowalski, J. A. Ph.D. Thesis, Stanford University, Stanford, CA, 2005, pp 31-109.
2. (b) He, W.; Cik, M.; Appendino, G.; Puyvelde, L. C.; Leysen, J. E.; De Kimpe, N. Mini-Rev. Med. Chem. 2002, 2, 185-200.
3. (c) Borris, R. P.; Blasko, G.; Cordell, G. A. J. Ethnopharmacol. 1988, 24, 41-92.
4. (d) Evans, F. J.; Soper, C. J. Lloydia 1978, 41, 193-233.
5. (a) Kupchan, S. M.; Sweeny, J. G.; Baxter, R. L.; Murae, T.; Zimmerly, V. A.; Sickles, B. R. J. Am. Chem. Soc. 1975, 97, 672-673.
6. Wender, P. A.; Jesudason, C. D.; Nakahira, H.; Tamura, N.; Tebbe, A. L.; Ueno, Y. J. Am. Chem. Soc. 1997, 119, 12976-12977.
7. For noteworthy synthetic approaches to daphnane diterpenes, see: (a) Jackson, S. R.; Johnson, M. G.; Mikami, M.; Shiokawa, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2001, 40, 2694-2697.
8. (b) Ritter, T.; Zarotti, P.; Carreira, E. M. Org. Lett. 2004, 6, 4371-4374.
9. (c) Page, P. C. B.; Hayman, C. M.; McFarland, H. L.; Willock, D. J.; Galea, N. M. Synlett 2002, 583-587.
10. For reviews, see: (a) Elitzin, V. I. Ph.D. Thesis, Stanford University. Stanford, CA, 2005, pp 50-96.
11. (b) Sammes, P. G. Gazz. Chim. Ital. 1986, 116, 109-114.
12. (c) Ohkata, K.; Akiba, K.-Y. Heterocycl. Chem. 1996, 65, 283-374.
13. (d) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1-85.
14. (e) Mascareñas, J. L. Adv. Cycloaddit. 1999, 6, 1-54.
15. For a definition and example, see: Wender, P. A.; Ternansky, R. J. Tetrahedron Lett. 1985, 22, 2625-2628.
16. For synthetic applications of oxidopyrylium-alkene cycloadditions from this laboratory, see: (a) Wender, P. A.; Lee, H. Y.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8954-8957.
17. (b) Wender, P. A.; Kogen, H.; Lee, H. Y.; Munger, J. D.; Wilhelm, R. S.; Williams, P. D. J. Am. Chem. Soc. 1989, 111, 8957-8958.
18. (c) Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956-4958.
19. (d) Wender, P. A.; Mascareñas, J. L. J. Org. Chem. 1991, 56, 6267-6269.
20. (e) Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
21. For recent examples, see: (a) Magnus, P.; Shen, L. Tetrahedron 1999, 55, 3553-3560.
22. (b) Magnus, P.; Waring, M. J.; Ollivier, C.; Lynch, V. Tetrahedron Lett. 2001, 42, 4947-4950.
23. (c) Ohmori, N. Chem. Commun. 2001, 1552-1553.
24. (d) Lopez, F.; Castedo, L.; Mascareñas, J. L. Chem. Eur. J. 2002, 8, 884-899.
25. (e) Baldwin, J. E.; Mayweg, A. V. W.; Pritchard, G. J.; Adlington, R. M. Tetrahedron Lett. 2003, 44, 4543-4545.
26. (t) Snider, B. B.; Grabowski, J. F. Tetrahedron Lett. 2005, 46, 823-825.
27. (a) Ohmori, N.; Yoshimura, M.; Ohkata, K. Heterocycles 1997, 45, 2097-2100.
28. (b) López, F.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2001, 3, 623-625.
29. (c) López, F.; Castedo, L.; Mascareñas, J. L. Org. Lett. 2002, 4, 3683-3685.
30. (d) Lopez, F.; Castedo, L.; Mascareñas, J. L. J. Org. Chem. 2003, 68, 9780-9786.
31. (e) Krishna, U. M.; Srikanth, G. S. C.; Trivedi, G. K.; Deodhar, K. D. Synlett 2003, 2383-2385.
32. (f) Krishna, U. M.; Deodhar, K. D.; Trivedi, G. K. Tetrahedron 2004, 60, 4829-4836.
33. Paquette, L. A.; Bailey, S. J. Org. Chem. 1995, 60, 7849-7856.
34. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016.
35. (a) Paterson, I.; Wallace, D .J.; Velázquez, S. M. Tetrahedron Lett. 1994, 35, 9083-9086.
36. (b) Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; González, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845-6848.
37. Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron Lett. 1986, 27, 3009-3012.
38. Paterson, I.; Lister, M. A.; Ryan, G. R. Tetrahedron Lett. 1991, 32, 1749-1752.
39. Ho, T.-L.; Sapp, S. G. Synth. Commun. 1983, 13, 207-211.
40. (a) Hyldtoft, L.; Madsen, R. J. Am. Chem. Soc. 2000, 122, 8444-8452.
41. (b) Stadmüller, H.; Lentz, R.; Tucker, C. E.; Stüdemann, T.; Dönner, W.; Knochel, P. J. Am. Chem. Soc. 1993, 115, 7027-7028.
42. Chemical derivatization followed of 27a followed by NOE analysis confirmed its stereochemistry as indicated. See the Supporting Information for details.