Sequential 1,2-addition-electrocyclic ring closures involving acyclic α,β-unsaturated iminiums: A formal [3 + 3] cycloaddition strategy to unique pyranyl spirocycles

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 690-691

  Hsung, Richard P ^a   Shen, Hong C ^a   Douglas, Christopher J ^a   Morgan, Christopher D ^a   Degen, Shane J ^a   Yao, Letitia J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; PYRONE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0033525090     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982165k     Document Type: Article

References (14)

1. Examples of [3 + 3] cycloaddition reactions in the truest sense are extremely scarce. There are limited examples of metal-mediated [3 + 3] cycloaddition reactions. For recent reviews, see: (a) Frühauf, H.-W. Chem. Rev. 1997, 97, 523. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Examples of formal [3 + 3] cycloaddition reactions in a stepwise manner are too vast to document.
2. Examples of [3 + 3] cycloaddition reactions in the truest sense are extremely scarce. There are limited examples of metal-mediated [3 + 3] cycloaddition reactions. For recent reviews, see: (a) Frühauf, H.-W. Chem. Rev. 1997, 97, 523. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49. Examples of formal [3 + 3] cycloaddition reactions in a stepwise manner are too vast to document.
3. For a leading reference with acyclic α,β-unsaturated aldehydes, see: de March, P.; Moreno-Mañas, M.; Casado, J.; Pleixats, R.; Roca, J. L.; Trius, A. J. Heterocycle. Chem. 1984, 21, 1369.
4. For examples of using cyclic enals: (a) Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888 (b) Jonassohn, M.; Sterner, O.; Anke, H. Tetrahedron 1996, 52, 1473.
5. For examples of using cyclic enals: (a) Hua, D. H.; Chen, Y.; Sin, H.-S.; Maroto, M. J.; Robinson, P. D.; Newell, S. W.; Perchellet, E. M.; Ladesich, J. B.; Freeman, J. A.; Perchellet, J.-P.; Chiang, P. K. J. Org. Chem. 1997, 62, 6888 (b) Jonassohn, M.; Sterner, O.; Anke, H. Tetrahedron 1996, 52, 1473.
6. For a leading reference, see: Otoguro, K.; Kuno, F.; Õmura, S. Pharmacol. Ther. 1997, 76, 45.
7. Obata, R.; Sunazuka, T.; Tian, Z.; Tomoda, H.; Harigaya, Y.; Õmura, S.; Smith, A. B., III. Chem. Lett. 1997, 935.
8. (a) Hsung, R. P. Heterocycles 1998, 48, 421.
9. (b) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
10. (c) Granum, K. G.; Merkel, G.; Mulder, J. A.; Debbins, S. A.; Hsung, R. P. Tetrahedron Lett. 1998, 9597.
11. For preparations of pyrones, see: Hsung, R. P.; Douglas, C. J.; Skelenica, H. Manuscript in preparation.
12. 13C NMR, FTIR, and mass spectroscopy.
13. 6,7a
14. For an example of this electrocyclic ring closure, see: Shishido, K.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1986, 971.