Biomimetic synthesis of a new class of bacterial signaling molecules

Organic Letters

Volumn 11, Issue 14, 2009, Pages 2984-2987

  Davis, Jesse B ^a   Bailey, J Daniel ^a   Sello, Jason K ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; MESYLIC ACID DERIVATIVE; SCANDIUM; SCANDIUM TRIFLATE;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; STREPTOMYCES COELICOLOR; SYNTHESIS;

BIOMIMETICS; CATALYSIS; FURANS; MESYLATES; MOLECULAR STRUCTURE; SCANDIUM; STREPTOMYCES COELICOLOR;

EID: 67650326845     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9009893     Document Type: Article

References (19)

1. Bassler, B. L.; Losick, R. Cell 2006, 125, 237-246.
2. Hopwood, D. A. Streptomyces in Nature and Medicine: The Antibiotic Makers; Oxford University Press: New York, 2007.
3. Corre, C.; Song, J.; O'Rourke, S.; Chater, K. F.; Challis, G. L. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 17510-17515.
4. Takano, E. Curr. Opin. Microbiol. 2006, 9, 287-294.
5. (a) Tietze, L. F.; Beifuss, U. The Knoevenagel Reaction. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 341-394.
6. (b) Tietze, L. F.; Rackelmann N. The Domino Knoevenagel-Hetero-Diels- Alder Reaction and Related Transformations. In Multicomponent Reactions; Zhu J., Bie, H., Eds.; WileyVCH: Weinheim, 2005; Vol. 12, pp 1-168.
7. Smith, M., March, J., Eds. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th ed.; John Wiley & Sons, Inc.: New York, 2001.
8. (a) Rao, P. S.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32, 5821-5822.
9. (b) Narsaiah, A. V.; Nagaiah, K. Synth. Commun. 2003, 33, 3825-3832.
10. The deprotection of acetals; is by scandium triflate is known. Oriyama, T.; Watahiki, T.; Kobayashi, Y.; Hirano, H.; Suzuki, T. Synth. Commun. 2001, 31, 2305-2311.
11. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
12. (a) Cane, D. E.; Yang, C. J. Am. Chem. Soc. 1987, 109, 12551257.
13. (b) Gilbert, I. H.; Ginty, M.; O'Neill, J. A.; Simpson, T. J.; Staunton, J.; Willis, C. L Bioorg. Med. Chem. Lett. 1995, 5, 1587-1590.
14. All reactions with the SNAC substrate were perfomed using THF as a solvent as the thioester was not sufficiently stable in methanol.
15. Kato, J.; Fuña, N.; Watanabe, H.; Ohnishi, Y.; Horinouchi, S. Proc Natl. Acad. Sci. U.S.A. 2007, 104, 2378-2383.
16. (a) Rodrigues, F.; Canac, Y.; Lubineau, A. Chem. Commun. 2000, 2049-2050.
17. (b) Bartoli, G.; Fernandez-Bolaos, J. G.; Di Antonio, G.; Foglia, G.; Giuli, S.; Gunella, R.; Mancinelli, M.; Marcantoni, E.; Paoletti, M. J. Org. Chem. 2007, 12, 6029-6036.
18. A furan methyl ester product was isolated from a zinc chloridecatalyzed reaction of hydroxyacetone and ethyl acetoacetate. Garcia Gonzalez, F. Adv. Carbohydr. Chem. 1956, 11, 97-143.
19. Kim, J.; Ashenhurst, J. A.; Movassaghi, M. Science 2009, 324, 238-241.