Stereoselective syntheses of 11-α-methoxycurvularin and 11-β-methoxycurvularin

Tetrahedron Letters

Volumn 50, Issue 28, 2009, Pages 4117-4120

  Venkateswar Reddy, G ^a   Sateesh Chandra Kumar, R ^a   Suresh Babu, K ^a   Madhusudana Rao, J ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

CBS reduction; Curvularins; Grubbs cross metathesis; Macrolides; Maruoka asymmetric allylation

Indexed keywords

11 ALPHA METHOXYCURVULARIN; 11 BETA METHOXYCURVULARIN; MACROLIDE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 66049092038     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.120     Document Type: Article

References (30)

1. Ju J., Rajski S.R., Lin S.-K., Seo J.-W., peters N.R., Hoffmann F.M., and Shen B. J. Am. Chem. Soc. 131 (2009) 1370
2. Kalz L., and Ashley G.W. Chem. Rev. 105 (2005) 499
3. Yoshino T., Ng F., and Danishefsky J. J. Am. Chem. Soc. 128 (2006) 14185
4. Ghosh A.K., and Gong G. J. Org. Chem. 77 (2006) 1085
5. Furster A., Castanet A.-S., Radkowski K., and Lehmann C.W. J. Org. Chem. 68 (2003) 1521 and referencec cited therein
6. Lai S., Shizuri Y., Yamamura S., Kawai K., and Furukawa H. Bull. Chem. Soc. Jpn. 64 (1991) 1048
7. He J., Wijeratne E.M.K., Bashyal B.P., Zhan J., Seliga C.J., Liu M.X., Pierson E.E., Pierson L.S., VanEtten H.D., and Gunatilaka A.A.L. J. Nat. Prod. 67 (2004) 1985
8. Zhan J., Wijeratne E.M.K., Seliga C.J., Pierson E.E., Pierson L.S., VanEtten H.D., and Gunatilaka A.A.L. J. Antibiot. 57 (2004) 341
9. Almassi F., Ghisalberti E.L., Skelton B.W., and White A.H. Aust. J. Chem. 47 (1994) 1193
10. Ghisalberti E.L., Hockless D.C.R., Rowland C.Y., and White A.H. Aust. J. Chem. 46 (1993) 571
11. Andreu J.M., and Timasheff S.N. Proc. Natl. Acad. Sci. U.S.A. 79 (1982) 6753
12. Hamel E. In: Avila de Grado J. (Ed). Microtubule Protiens (1989), CRC, Boca Raton, FL
13. Liang Q., Sun Y., Yu B., She X., and Pan X. J. Org. Chem. 72 (2007) 9846
14. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019
15. Hanawa H., Hashimoto T., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 1708
16. Chandrasekhar S., Narsihmulu Ch., Sultana S.S., and Reddy M.S. Tetrahedron Lett. 45 (2004) 9299
17. Enantiomeric excess (ee) of the Homoallyl alcohol 14a determined by chiral HPLC [Chiral Pak-IA, 250X 4.6 mm, iPrOH/hexane (5:95), flow rate 1.0 ml/min, RT = 9.251(1.02%), 7.695 (98.98%)].
18. BouzBouz S., Simmons R., and Cossy J. Org. Lett. 6 (2004) 3465 and references cited therein
19. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551
20. Corey .J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986
21. The diastereoselectivity was determined by HPLC [Chiral Pak IA, Chiral Pak-IA, 250X 4.6 mm, 5 μ], flow rate: 1.0 mL/min, 210 nm, eluent, iPrOH/hexane 3:97, retention time: 16.24 min.
22. Baker P.M., Bycroft B.W., and Roberts J.C. J. Chem. Soc. (C) (1967) 1913
23. McNeill A.H., and Thomas E.J. Tetrahedron Lett. 34 (1993) 1669
24. Bowden k., Heilbron I.M., Jones E.R.H., and Weedon B.C.L. J. Chem. Soc. (1946) 39
25. Bowers A., Halsall T.G., Jones E.R.H., and Lemin A.J. J. Chem. Soc. (1953) 2548
26. Bracher F., and Schulte B. Liebigs Ann. Recl. (1997) 1979
27. Liang Q., Zhang J., Quan W., Sun Y., She X., and Pan X. J. Org. Chem. 72 (2007) 2694
28. Bringmann G., Lang G., Michel M., and Heubes M. Tetrahedron Lett. 45 (2004) 2829
29. Kreipl A.T., Reid C., and Steglich W. Org. Lett. 4 (2002) 3287
30. 6, 443.2434).