Transannular Nitrone Cycloaddition. A Stereocontrolled Entry to the Spirocyclic Core of Pinnaic Acid

Organic Letters

Volumn 3, Issue 3, 2001, Pages 413-415

  White, James D ^a   Blakemore, Paul R ^a   Korf, Eric A ^a   Yokochi, Alexandre F T ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; NITROGEN OXIDE; NITRONES; PINNAIC ACID; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; CRYSTALLOGRAPHY, X-RAY; NITROGEN OXIDES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0035825771     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000361j     Document Type: Article

References (30)

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2. For some recent examples, see: (a) Marsault, E.; Deslongchamps, P. Org. Lett. 2000, 2, 3317. (b) Toro, A.; L'Heureux, A.; Deslongchamps, P. Org. Lett. 2000, 2, 2737. (c) Lavoie, R.; Ouellet, S. G.; Dallaire, C.; Dory, Y. L.; Toro, A.; Deslongchamps, P. Tetrahedron 2000, 56, 5509. (d) Frank, S. A.; Works, A. B.; Roush, W. R. Can. J. Chem. 2000, 78, 757. (e) Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
3. For some recent examples, see: (a) Marsault, E.; Deslongchamps, P. Org. Lett. 2000, 2, 3317. (b) Toro, A.; L'Heureux, A.; Deslongchamps, P. Org. Lett. 2000, 2, 2737. (c) Lavoie, R.; Ouellet, S. G.; Dallaire, C.; Dory, Y. L.; Toro, A.; Deslongchamps, P. Tetrahedron 2000, 56, 5509. (d) Frank, S. A.; Works, A. B.; Roush, W. R. Can. J. Chem. 2000, 78, 757. (e) Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
4. For some recent examples, see: (a) Marsault, E.; Deslongchamps, P. Org. Lett. 2000, 2, 3317. (b) Toro, A.; L'Heureux, A.; Deslongchamps, P. Org. Lett. 2000, 2, 2737. (c) Lavoie, R.; Ouellet, S. G.; Dallaire, C.; Dory, Y. L.; Toro, A.; Deslongchamps, P. Tetrahedron 2000, 56, 5509. (d) Frank, S. A.; Works, A. B.; Roush, W. R. Can. J. Chem. 2000, 78, 757. (e) Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
5. For some recent examples, see: (a) Marsault, E.; Deslongchamps, P. Org. Lett. 2000, 2, 3317. (b) Toro, A.; L'Heureux, A.; Deslongchamps, P. Org. Lett. 2000, 2, 2737. (c) Lavoie, R.; Ouellet, S. G.; Dallaire, C.; Dory, Y. L.; Toro, A.; Deslongchamps, P. Tetrahedron 2000, 56, 5509. (d) Frank, S. A.; Works, A. B.; Roush, W. R. Can. J. Chem. 2000, 78, 757. (e) Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
6. For some recent examples, see: (a) Marsault, E.; Deslongchamps, P. Org. Lett. 2000, 2, 3317. (b) Toro, A.; L'Heureux, A.; Deslongchamps, P. Org. Lett. 2000, 2, 2737. (c) Lavoie, R.; Ouellet, S. G.; Dallaire, C.; Dory, Y. L.; Toro, A.; Deslongchamps, P. Tetrahedron 2000, 56, 5509. (d) Frank, S. A.; Works, A. B.; Roush, W. R. Can. J. Chem. 2000, 78, 757. (e) Toro, A.; Nowak, P.; Deslongchamps, P. J. Am. Chem. Soc. 2000, 122, 4526.
7. For a recent example, see: White, J. D.; Kim, J.; Drapela, N. E. J. Am. Chem. Soc. 2000, 122, 8665.
8. Transannular nitrone cycloadditions in which the nitrone is external to the ring have been reported: (a) Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskokovic, M.J. Am. Chem. Soc. 1982, 104, 6460. (b) Mihailovic, M. L.; Rajkovic, M. M.; Lorenc, L. B.; Pavlovic, V. D.; Milovanovic, A. Z.; Tinant, B.; Declercq, J.-P. Tetrahedron 1996, 52, 11995.
9. Transannular nitrone cycloadditions in which the nitrone is external to the ring have been reported: (a) Baggiolini, E. G.; Lee, H. L.; Pizzolato, G.; Uskokovic, M.J. Am. Chem. Soc. 1982, 104, 6460. (b) Mihailovic, M. L.; Rajkovic, M. M.; Lorenc, L. B.; Pavlovic, V. D.; Milovanovic, A. Z.; Tinant, B.; Declercq, J.-P. Tetrahedron 1996, 52, 11995.
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12. For alternative approaches to the azaspirocyclic core of pinnaic acid, see: (a) Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1999, 40, 3583. (b) Koviach, J. L.; Forsyth, C. J. Tetrahedron Lett. 1999, 40, 8529. (c) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503. (d) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542. (e) Lee, S.; Zhao, Z. Tetrahedron Lett. 1999, 40, 7921. (f) Shindo, M.; Fukuda, Y.; Shishido, K. Tetrahedron Lett. 2000, 41, 929. (g) Wright, D. L.; Schulte, J. P.; Page, M. A. Org. Lett. 2000, 2, 1847.
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14. For alternative approaches to the azaspirocyclic core of pinnaic acid, see: (a) Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1999, 40, 3583. (b) Koviach, J. L.; Forsyth, C. J. Tetrahedron Lett. 1999, 40, 8529. (c) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503. (d) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542. (e) Lee, S.; Zhao, Z. Tetrahedron Lett. 1999, 40, 7921. (f) Shindo, M.; Fukuda, Y.; Shishido, K. Tetrahedron Lett. 2000, 41, 929. (g) Wright, D. L.; Schulte, J. P.; Page, M. A. Org. Lett. 2000, 2, 1847.
15. For alternative approaches to the azaspirocyclic core of pinnaic acid, see: (a) Arimoto, H.; Asano, S.; Uemura, D. Tetrahedron Lett. 1999, 40, 3583. (b) Koviach, J. L.; Forsyth, C. J. Tetrahedron Lett. 1999, 40, 8529. (c) Clive, D. L. J.; Yeh, V. S. C. Tetrahedron Lett. 1999, 40, 8503. (d) Trauner, D.; Schwarz, J. B.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1999, 38, 3542. (e) Lee, S.; Zhao, Z. Tetrahedron Lett. 1999, 40, 7921. (f) Shindo, M.; Fukuda, Y.; Shishido, K. Tetrahedron Lett. 2000, 41, 929. (g) Wright, D. L.; Schulte, J. P.; Page, M. A. Org. Lett. 2000, 2, 1847.
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