De novo formal synthesis of (-)-virginiamycin M2 via the asymmetric hydration of dienoates

Organic Letters

Volumn 9, Issue 16, 2007, Pages 3105-3108

  Mortensen, Matthew S ^a   Osbourn, Joshua M ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; MACROLIDE; UNCLASSIFIED DRUG; VIRGINIAMYCIN; VIRGINIAMYCIN M2;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; MACROLIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; VIRGINIAMYCIN;

EID: 34547927646     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071145e     Document Type: Article

References (34)

1. (a) Walsh, C. T. Nature 2000, 406, 775-781.
2. (b) Chang, S.; Sievert, D. M.; Hageman, J. C.; Boulton, M. L.; Tenover, F. C.; Downes, F. P.; Shah, S.; Rudrik, J. T.; Pupp, G. R.; Brown, W. J.; Cardo, D.; Fridkin, S. K. New Engl. J. Med. 2003, 348, 1342-1349 and refs therein.
3. (c) Manthous, C. A.; Amaoteng-Adjepong, Y. Chest 2000, 118, 9-11. For clinical and pharmacological background on streptomycin antibiotics, see:
4. (d) Barriere, J. C.; Berthaud, N.; Beyer, D.; Dutka-Malen, S.; Paris, J. M.; Desnottes, J. F. Curr. Pharm. Des. 1998, 4, 155-180.
5. (e) Manzella, J. P. Am. Fam. Physician 2001, 64, 1863-1866.
6. (f) Mukhtar, T. A.; Wright, G. D. Chem. Rev. 2005, 105, 529-542.
7. (g) Porse, B. T.; Garrett, R. A. J. Mol. Biol. 1999, 286, 375. For synthesis of new quinolone class antibiotic active against VRSA, see:
8. (h) de Souza, N. J.; Gupte, S. V.; Deshpande, P. K.; Desai, V. N.; Bhawsar, S. B.; Yeole, R. D.; Shukla, M. C.; Strahilevitz, J.; Hooper, D. C.; Bozdogan, B.; Applebaum, P. C.; Jacobs, M. R.; Shetty, N.; Patel, M. V.; Jha, R.; Khorakiwala, H. F. J. Med. Chem. 2005, 48, 5232-5242.
9. McCaughey, B. N.Y. Times Nov 14, 2006, p 27.
10. Schito, G. C. Clin. Microbiol. Infect. 2006, 12, 3-8.
11. For conformational studies of the virginiamycin type antibiotics, see: (a) Dang, J.; Metzger, R. P.; Brownlee, R. T. C.; Chai, A. N.; Separovic, F. Eur. J. Biophys. 2005, 34, 383-388.
12. (b) Dang, J.; Separovic, F.; Brownlee, R. T. C.; Metzger, R. P. J. Org. Biomol. Chem. 2004, 2, 2919-2924.
13. (c) Dang, J.; Separovic, F.; Brownlee, R. T. C.; Metzger, R. P. Aust. J. Chem. 2004, 57, 415-418.
14. 2, see: (a) Schlessinger, R. H.; Li, Y.-J. J. Am. Chem. Soc 1996, 118, 3301-3302. For the second, see:
15. (b) Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149-3152.
16. For the first total synthesis of madumycin II, see: (c) Tavares, F.; Lawson, J. P.; Meyers A. I. J. Am. Chem. Soc. 1996, 118, 3303-3304.
17. For the second, see: (d) Ghosh, A. K.; Liu, W. J. Org. Chem. 1997, 62, 7908-7909.
18. Brennan, C. J.; Campagne, J.-M. Tetrahedron Lett. 2001, 42, 5195-5197.
19. The regioselectivity of the asymmetric dihydroxylation of di- and trienoates has been studied by Sharpless. See: (a) Berker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345-1376. Our group:
20. (b) Zhang, Y.; O'Doherty, G. A. Tetrahedron 2005, 61, 6337-6351.
21. For the use of this approach in synthesis, see: (a) Smith, A. B.; Walsh, S. P.; Frohn, M.; Duffey, M. O. Org. Lett. 2005, 7, 139-142.
22. (b) Ahmed, Md. M.; Akhmedov, N.; Cui, H.; Friedrich, D.; O'Doherty, G. A. Heterocycles 2006, 70, 223-233.
23. (c) Ahmed, Md. M.; Cui, H.; O'Doherty, G. A. J. Org. Chem. 2006, 71, 6686-6689.
24. (d) Gao, D.; O'Doherty, G. A. J. Org. Chem. 2005, 70, 9932-9939.
25. (e) Ahmed, Md. M.; O'Doherty, G. A. Tetrahedron Lett. 2005, 46, 4151-4155.
26. (a) Ahmed, Md.; Mortensen, M. M. S.; O'Doherty, G. A. J. Org. Chem. 2006, 71, 7741-7746.
27. (b) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 1049-1052.
28. For its use in the synthesis of natural products, see: (c) Li, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 3987-3990.
29. (d) Li, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 6087-6090.
30. We have found this acid-catalyzed isomerization of α,β- unsaturated aldehydes to be quite general and very useful in our diene syntheses. See: Varelis, P.; Johnson, B. Aust. J. Chem. 1997, 50, 43-52.
31. In addition to the electronic effect, we have found that subtle steric effects can lead to the formation of regioisomers in the Sharpless asymmetric dihydroxylation reaction of dienoates. See refs 7 and 9a.
32. 3 reduction of dienylnitriles like 21 is precedented; see ref 5a.
33. We surmised that this lower than expected yield was due to the water solubility of 25; no elimination to dienoate 8 was observed.
34. 13C NMR spectral data. The remaining 25 signals above 24 ppm did match the reported data; see ref 5a.