A facile synthesis of the basic steroidal skeleton using a Pauson-Khand reaction as a key step

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8264-8267

  Kim, Do Han ^a   Kim, Kwang ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

FACILE SYNTHESIS; NUCLEOPHILIC ADDITION; PAUSON-KHAND REACTION;

ADDITION REACTIONS; CARBONYLATION; MOLECULAR DYNAMICS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

STEROID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DIASTEREOISOMER; PAUSON KHAND REACTION; STEREOCHEMISTRY; STEROIDOGENESIS; STOICHIOMETRY;

EID: 33749993154     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061052v     Document Type: Article

References (28)

1. Pauson, P. L.; Khand, I. U.; Knox, G. R.; Watts, W. E. J. Chem. Soc. D 1971, 36.
2. For recent reviews, see: (a) Park, K. H.; Chung, Y. K. Synlett 2005, 545.
3. (b) Rodriguez Rivero, M.; Adrio, J.; Carretero, J. C. Synlett 2005, 26.
4. (c) Gibson, S. E.; Mainolfi, N. Angew. Chem., Int. Ed. 2005, 44, 3022.
5. (d) Bonaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
6. (e) Hanson, B. E. Comments Inorg. Chem. 2002, 23, 289.
7. (f) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
8. Krafft, M. E.; Dasse, O. A.; Shao, B. Tetrahedron 1998, 54, 7033.
9. (a) Pattenden, G.; Gonzalez, M. A.; McCulloch, S.; Walter, A.; Woodhead, S. J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12024 and references therein.
10. (b) Nagyar, A.; Wolfling, J.; Kubas, M.; Seijo, J. A. C.; Sevvana, M.; Herbst-Imer, R.; Forgo, P.; Schneider, G. Steroids 2004, 69, 301.
11. (c) Pattenden, G.; Reddy, L. K.; Walter, A. Tetrahedron Lett. 2004, 45, 4027.
12. (d) Hu, Q. Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984.
13. (a) Sünnemann, H. W.; de Meijere, A. Angew. Chem., Int. Ed. 2004, 43, 895.
14. (b) Skoda-Földes, R.; Kollár, L. Chem. Rev. 2003, 103, 4095.
15. (c) Wu, H. P.; Aumann, R.; Frolich, R.; Wibbeling, B. Chem.-Eur. J. 2002, 8, 910.
16. (d) Aumann, R.; Meyer, A. G.; Frohlich, R. J. Am. Chem. Soc. 1996, 118, 10853.
17. (e) Wender, P. A.; Smith, T. E. J. Org. Chem. 1995, 60, 2962.
18. (a) Petit, M.; Aubert, C.; Malacria, M. Org. Lett. 2004, 6, 3937.
19. (b) Michellys, P. Y.; Marin, P.; Toupet, L.; Pellissier, H.; Santelli, M. J. Org. Chem. 2001, 66, 115.
20. (c) Tietze, L. F.; Nöbel, T.; Spescha, M. J. Am. Chem. Soc. 1998, 120, 8971.
21. (a) Park, K. H.; Son, S. U.; Chung, Y. K. Adv. Synth. Catal. 2005, 347, 854.
22. (b) Kim, D. H.; Chung, Y. K. Chem. Commun. 2005, 1634.
23. (c) Park, K. H.; Son, S. U.; Chung, Y. K. Org. Lett. 2004, 6, 1183.
24. (a) Fürstner, A.; Hannen, P. Chem.-Eur. J. 2006, 12, 3006.
25. (b) Bartoli, G.; Bosco, M.; Di Martino, E.; Marcantoni, E.; Sambri, L. Eur. J. Org. Chem. 2001, 2901.
26. (c) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Pharm. Bull. 1986, 34, 1531.
27. (d) Liu, H.-J.; Shia, K.-S.; Shang, X.; Zhu, B.-Y. Tetrahedron 1999, 55, 3803.
28. o > 2.0σ(I).