Stereoselective synthesis of polyhydroxylated indolizidines based on pyridinium salt photochemistry and ring rearrangement metathesis

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7284-7293

  Song, Ling ^a   Duesler, Eileen N ^a   Mariano, Patrick S ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENZYME INHIBITION; PHOTOCHEMICAL REACTIONS; RUTHENIUM; SALTS; SYNTHESIS (CHEMICAL);

HIGH YIELD; REARRANGEMENT METATHESIS; REGIOSELECTIVITY;

ORGANIC COMPOUNDS;

CYCLOPENTENE DERIVATIVE; GLYCOSIDASE INHIBITOR; INDOLIZIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; RUTHENIUM; SWAINSONINE;

ARTICLE; CATALYSIS; HYDROXYLATION; PHOTOCHEMISTRY; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; INDOLIZINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTOCHEMISTRY; PYRIDINIUM COMPOUNDS; STEREOISOMERISM;

EID: 5444267441     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040226a     Document Type: Article

References (32)

1. Kaplan, L.; Pavlik, J. W.; Wilzbach, K. E. J. Am. Chem. Soc. 1972, 94, 3283.
2. Yoon, U. C.; Quillen, S. L.; Mariano, P. S.; Swanson, R.; Stavinoha, J. L.; Bay, E. J. Am. Chem. Soc. 1983, 105, 1204.
3. Ling, R.; Yoshida, M.; Mariano, P. S. J. Org. Chem. 1996, 61, 4439.
4. Ling, R.; Mariano, P. S. J. Org. Chem. 1998, 63, 6072. A newly developed procedure for hydrolytic ring opening of the oxazoline, formed by treatment of 3 and related substances with the Burgess salt, was used in this case (see the description of the process used to transform 19 to 20).
5. (a) Cho, S. J.; Ling, R.; Kim, A.; Mariano, P. S. J. Org. Chem. 2000, 65, 1574.
6. (b) Lu, H.; Mariano, P. S.; Lam, Y. F. Tetrahedron Lett. 2001, 42, 4755.
7. Lu, H.; Su, Z.; Song, L.; Mariano, P. S. J. Org. Chem. 2002, 67, 3525.
8. Zuercher, W. J.; Hashimoto, M.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 6634.
9. Stragies, R.; Blechert, S, Synlett 1998, 169. Stragies, R.; Blechert, S. J. Am. Chem. Soc. 2000, 122, 9584.
10. Stragies, R.; Blechert, S, Synlett 1998, 169. Stragies, R.; Blechert, S. J. Am. Chem. Soc. 2000, 122, 9584.
11. For a recent review see: Randl, S.; Blechert, S. In Hanbook of Metathesis. Applications in Organic Synthesis; Grubbs, R. H., Ed.; Wiley-VCH: Morlenbach, 2003; Vol. 2.
12. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
13. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674.
14. Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Smith, A. B.; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 123, 990.
15. Miller, S. J.; Kim, S. H.; Chen, Z. R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108. Smith, A. B.; Adams, C. M.; Kozmin, S. A. J. Am. Chem. Soc. 2001, 123, 990.
16. Ovaa, H.; Stapper, C.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H.; Blechert, S. Tetrahedron 2002, 58, 7503.
17. Harrity, J. P. A.; Visser, M. S.; Gleason, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 1488.
18. Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343.
19. Observation suggesting that RRM reactions of terminal-alkenyl-substituted cycloalkenes are intiated by metathesis at the terminal olefinic center is found in refs 7 and 13.
20. Steric arguments such as the one presented here have been used by Snapper (Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 1478) to explain the regiochemical course of cross metathesis reactions of fused cyclobutenes.
21. For other recent approaches to the synthesis of N-heterocycles relying on RRM reactions, see: Stragies, R.; Blechert, S. Tetrahedron 1999, 55, 8179.
22. Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. Buschmann, N.; Ruckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325.
23. Voigtmann, U.; Blechert, S. Org. Lett. 2000, 2, 3971. Buschmann, N.; Ruckert, A.; Blechert, S. J. Org. Chem. 2002, 67, 4325.
24. For a description of a recent synthesis of (-)-swainsonine as well as references to earlier work, see: Pearson, W. H.; Ren, Y.; Powers, J. D. Heterocycles 2002, 58, 421.
25. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943. Cha, J. K.; Kim, N. S. Chem. Rev. 1995, 95, 1761.
26. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943. Cha, J. K.; Kim, N. S. Chem. Rev. 1995, 95, 1761.
27. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768.
28. Marshall, J. A.; Tang, Y. J. Org. Chem. 1994, 59, 1457.
29. Lindsay, K. B.; Pyne, S. G. J. Org. Chem. 2002, 67, 7774.
30. Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
31. Elbein, A. D.; Szumilo, T.; Sanford, B. A.; Sharpless, K. B.; Adams, C. Biochemistry 1987, 26, 2502.
32. 1H NMR spectrum of 68 was kindly provided by C. Adams.