A Convenient One-Pot Procedure to Afford Bicyclic Molecules by Stereospecific Iron Carbonyl Mediated [6 + 2] Ene-Type Cyclization: A Possible Approach to Gelsemine

Journal of the American Chemical Society

Volumn 125, Issue 44, 2003, Pages 13326-13327

  Pearson, Anthony J ^a   Wang, Xiaolong ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CARBONYL IRON; GELSEMINE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; CYCLOADDITION; ISOMERISM; STEREOSPECIFICITY; SYNTHESIS;

ALKALOIDS; ALKENES; BICYCLO COMPOUNDS; CYCLIZATION; STEREOISOMERISM;

EID: 0242330821     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030407e     Document Type: Article

References (21)

1. (a) Hegedus, L. S. In Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; Universtiy Science Books: Sausalito, California, 1999.
2. (b) Pearson, A. J. Iron Compounds in Organic synthesis; Academic Press: San Diego, 1994.
3. (a) Stille, J. K.; Becker, Y. J. Org. Chem. 1980, 45, 2139.
4. (b) Uma, R.; Crevisy, C. Grée, R. Chem. Rev. 2003, 103, 27.
5. Dieck, H. T.; Dietrich, J.; Wilke, G. Angew. Chem. 1985, 97, 795.
6. (a) Pearson, A. J.; Zettler, M. J. Am. Chem. Soc. 1989, 111, 3908.
7. (b) Pearson, A. J.; Dorange, I. B. J. Org. Chem. 2001, 66, 3140.
8. (c) Pearson, A. J.; Wang, X. Tetrahedron Lett. 2002, 43, 7513.
9. (d) Pearson, A. J.; Wang, X. J. Am. Chem. Soc. 2003, 125, 638.
10. For other metal catalyzed [6 + 2] cyclizations, see for example: (e) Rigby, J. H.; Kondratenko, M. A.; Fiedler, C. Org. Lett. 2000, 2, 3917.
11. (f) Schmidt, T.; Bienewald, F.; Goddard, R. Chem. Commun. 1994, 16, 1857.
12. Bandara, B. M. R.; Birch, A. J.; Raverty, W. D. J. Chem. Soc., Perkin Trans. 1 1982, 1755.
13. See for example: (a) Ng, F. W.; Lin, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 9812.
14. (b) Madin, A.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. Angew. Chem., Int. Ed. 1999, 38, 2934.
15. Bandara, B. M. R.; Birch, A. J.; Raverty, W. D. J. Chem. Soc., Perkin Trans. 1 1982, 1763.
16. Ganem, B.; Holbert, G. W.; Weiss, L. B.; Ishizumi, K. J. Am. Chem. Soc. 1978, 100, 6483.
17. Mander, L. N.; Williams, C. M. Tetrahedron 2003, 59, 1105.
18. (a) Bäckvall, J. E.; Vagberg, J.; Nordberg, R. E. Tetrahedron Lett. 1984, 25, 2717.
19. (b) Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593.
20. 3 disengaged from the diene due to steric hindrance of the isopropyl and recoordinated to the diene on the other face during the reaction.
21. Bandara, B. M. R.; Birch, A. J.; Chauncy, B.; Kelly, L. F. J. Organomet. Chem. 1981, 208, 332.