An efficient asymmetric synthesis of manzacidin C

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3165-3167

  Tran, Kristy ^a   Lombardi, Pamela J ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MANZACIDIN C; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; MOLECULAR STRUCTURE; PYRIMIDINES; PYRROLES; STEREOISOMERISM;

EID: 52049111424     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8011869     Document Type: Article

References (19)

1. Kobayashi, J.; Kanda, F.; Ishibashi, M.; Shigemori, H. J. Org. Chem. 1991, 56, 4574.
2. Jahn, T.; König, G. M.; Wright, A. D. Tetrahedron Lett. 1997, 38, 3883.
3. For a summary and lead references, see: Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113.
4. Hashimoto, T.; Maruoka, K. Org. Biomol. Chem. 2008, 6, 829.
5. Namba, K.; Shinada, T.; Teramoto, T.; Ohfune, Y. J. Am. Chem. Soc. 2000, 122, 10708.
6. (a) Wehn, P. M.; Du Bois, J. J. Am. Chem. Soc. 2002, 124, 12950.
7. (b) Kano, T.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2006, 128, 2174.
8. (c) Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928.
9. (d) Sibi, M. P.; Stanley, L. M.; Soeta, T. Org. Lett. 2007, 9, 1553.
10. (a) Lanter, J. C.; Chen, H.; Zhang, X.; Sui, Z. Org. Lett. 2005, 7, 5905.
11. (b) Wang, B.; Wu, F.; Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2007, 129, 768.
12. Drouin, C.; Woo, J. C. S.; MacKay, D. B.; Lavigne, R. M. A. Tetrahedron Lett. 2004, 45, 7197.
13. Shinada, T.; Ikebe, E.; Oe, K.; Namba, K.; Kawasaki, M.; Ohfune, Y. Org. Lett. 2007, 9, 1765.
14. Shirakawa, S.; Lombardi, P. J.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 9974.
15. Notte, G. T.; Leighton, J. L. J. Am. Chem. Soc. 2008, 130, 6676.
16. The relative and absolute stereochemistry of the diastereomers of 6 has not been rigorously established.
17. We have established a stepwise mechanism for the acylhydrazoneenol ether cycloaddition reaction. See ref 10.
18. This result was unexpected and is a reversal of the absolute sense of induction observed when hydrazone 4 is engaged in Friedel-Crafts reactions (see : Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 2858). The mechanistic basis for this reversal, possibly associated with the use of AgOTf, is under investigation.
19. A similar cyclization was carried out by Du Bois and Wehn, and they describe similar observations. See ref 6a.