Stereoselective synthesis (+)-cephalosporolide D

Tetrahedron Letters

Volumn 51, Issue 13, 2010, Pages 1723-1726

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

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

CBS reduction; Cephalosporolide D; Fungal metabolites; Grubb's cross metathesis; Maruoka asymmetric allylation; Yamaguchi macrolactonization

Indexed keywords

CEPHALOSPOROLIDE D; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; COST EFFECTIVENESS ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; LACTONIZATION; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 76949095154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.082     Document Type: Article

References (29)

1. For a recent review, see:. Rosseau G. Tetrahedron 51 (1995) 2777
2. Ackland M.J., Hanson J.R., Hitchcock, and Ratcliffe A.H. J. Chem. Soc., Perkin. Trans 1 (1985) 843
3. Shiina I., Hashizume M., Yamai Y., Oshiumi H., Shimazaki T., Takasuma Y., and Ibuka R. Tetrahedron Lett. 45 (2004) 543
4. Buszek K.R., Jeong Y., Sato N., Still P.C., Muino P.L., and Ghosh I. Synth. Commun. 31 (2001) 1781
5. Shiina I., Hashizume M., Yamai Y., Oshiumi H., Shimazaki T., Takasuma Y., and Ibuka R. Chem. Eur. J. 11 (2005) 6601
6. Shiina I., Fukuda Y., Ishii T., Fujisawa H., and Mukaiyama T. Chem. Lett. (1998) 831
7. Shiina I., Fujisawa H., Ishii T., and Fukuda Y. Heterocycles 52 (2000) 1105
8. Shiina I. Chem. Rev. 107 (2007) 239
9. Kumar R.S.C., Sreedhar E., Reddy G.V., Babu K.S., and Rao J.M. Tetrahedron: Asymmetry 20 (2009) 1160
10. Sreedhar E., Kumar R.S.C., Reddy G.V., Robinson A., Babu K.S., and Rao J.M. Tetrahedron: Asymmetry 20 (2009) 440
11. Reddy G.V., Kumar R.S.C., Babu K.S., and Rao J.M. Tetrahedron Lett. 50 (2009) 4117
12. Kumar R.S.C., Reddy G.V., Shankariah G., Babu K.S., and Rao J.M. Tetrahedron Lett. 51 (2010) 1114
13. Inanaga J., Harata K., Saeki H., Katsaki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989
14. Solladle-Cavallo A., and Bonne F. Tetrahedron: Asymmetry 7 (1996) 171
15. Freeman F., and Kim D.S.H.L. J. Org. Chem. 57 (1992) 1722
16. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019
17. Hanawa H., Hashimoto T., and Maruoka K. J. Am. Chem. Soc. 125 (2003) 1708
18. Chandrasekhar S., Narsihmulu Ch., Sultana S.S., and Reddy M.S. Tetrahedron Lett. 45 (2004) 9299
19. The enantiomeric excess (ee) of the homoallyl alcohol 14 was determined by HPLC [Diacel OD-H column, 250 × 4.6 mm, 5 μ, 254 nm; eluent, 2% (0.1% of DMA) ethanol, 98% hexane, 20 μL injection volume, flow rate 0.5 mL/min retention time 9.39 and 10.46 min].
20. Stork G., and Takahashi T. J. Am. Chem. Soc. 99 (1977) 1275
21. BouzBouz S., Simmons R., and Cossy J. Org. Lett. 6 (2004) 3465 and references cited therein
22. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551
23. Corey J., and Helal C.J. Angew. Chem., Int. Ed. 37 (1998) 1986
24. The diastereoselectivity was determined by HPLC [Diacel OD-H column, 250 × 4.6 mm, 5 μ, 225 and 254 nm; eluent, 5% (0.1% of DMA) ethanol, 95% hexane, 20 μL injection volume, flow rate 1 mL/min retention time 3.1 and 4.3 min].
25. De Mico A., Margarita R., Parlanti L., Vescovi A., and Piancatelli G. J. Org. Chem. 62 (1997) 6974
26. Epp J.B., and Widlanski T.S. J. Org. Chem. 64 (1999) 293
27. McNeill A.H., and Thomas E.J. Tetrahedron Lett. 34 (1993) 1669
28. Meyers A.I., Durandetta J.L., and Munavu R. J. Org. Chem. 40 (1975) 2025
29. 5: 243.1208; found: 243.1200.