Ring-Closing Metathesis of Enynes Tethered by an N-O Bond: Synthesis of 1,2-Oxaza Polycycles by Diels-Alder Reaction of the Ring-Closing Metathesis Products

Synlett

Volumn , Issue 13, 2003, Pages 2017-2020

  Yang, Young Keun ^a   Tae, Jinsung ^a  

^a Yonsei University   (South Korea)

Author keywords

Cyclizations; Diels Alder reaction; Enynes; Metathesis; Ruthenium

Indexed keywords

1,2 OXAZAHETEROCYCLIC COMPOUND; ALKADIENE; AROMATIC COMPOUND; ENYNE; HETEROCYCLIC COMPOUND; NITROGEN; OXYGEN; POLYCYCLIC AROMATIC COMPOUND; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0242351861     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42038     Document Type: Article

References (23)

1. For reviews on enyne-metathesis, see: (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (b) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
2. For reviews on enyne-metathesis, see: (a) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1. (b) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
3. For recent examples of ring-closing enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441. (b) Stephen, C. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (c) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231. (d) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (e) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101. (f) Stephen, C. J.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 23, 2629.
4. For recent examples of ring-closing enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441. (b) Stephen, C. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (c) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231. (d) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (e) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101. (f) Stephen, C. J.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 23, 2629.
5. For recent examples of ring-closing enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441. (b) Stephen, C. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (c) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231. (d) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (e) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101. (f) Stephen, C. J.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 23, 2629.
6. For recent examples of ring-closing enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441. (b) Stephen, C. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (c) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231. (d) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (e) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101. (f) Stephen, C. J.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 23, 2629.
7. For recent examples of ring-closing enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441. (b) Stephen, C. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (c) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231. (d) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (e) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101. (f) Stephen, C. J.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 23, 2629.
8. For recent examples of ring-closing enyne metathesis, see: (a) Poulsen, C. S.; Madsen, R. J. Org. Chem. 2002, 67, 4441. (b) Stephen, C. J.; Elustondo, F.; Trevitt, G. P.; Boyall, D.; Robertson, J.; Blake, A. J.; Wilson, C.; Stammen, B. Tetrahedron 2002, 58, 1973. (c) Timmer, M. S. M.; Ovaa, H.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8231. (d) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (e) Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101. (f) Stephen, C. J.; Trevitt, G. P.; Boyall, D.; Stammen, B. Chem. Commun. 1998, 23, 2629.
9. For reviews on metathesis, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
10. For reviews on metathesis, see: (a) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
11. Yao, Q. Org. Lett. 2001, 3, 2069.
12. Micalizio, G. C.; Schreiber, S. L. Angew. Chem. Int. Ed. 2002, 41, 152.
13. Hoye, T. R.; Donaldson, S. M.; Vos, T. J. Org. Lett. 1999, 1, 277.
14. (a) Koeanig, S. G.; Leonard, K. A.; Lwe, R. S.; Austin, D. J. Tetrahedron Lett. 2000, 41, 9393.
15. (b) Cicchi, S.; Bonanni, M.; Cardona, F.; Revuelta, J.; Goti, A. Org. Lett. 2003, 5, 1773; and references cited therein.
16. Schreiber, S. L. Science 2000, 287, 1964.
17. Yang, Y.-K.; Tae, J. Synlett 2003, 1043.
18. For related RCM of hydroxylamine-tethered dienes, see: (a) Koide, K.; Finkelstein, Z. B.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398. (b) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
19. For related RCM of hydroxylamine-tethered dienes, see: (a) Koide, K.; Finkelstein, Z. B.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398. (b) Miyabe, H.; Yoshida, K.; Matsumura, A.; Yamauchi, M.; Takemoto, Y. Synlett 2003, 567.
20. We have observed spontaneous oxidation of compounds 18 and 19 to the corresponding aromatic compounds 30 and 32 within a few days after preparation under the standard storage conditions.
21. Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375.
22. 3: 211.1208; found: 211.1206.
23. 7: 353.1475; found: 353.1485.