First total syntheses of (3 R,5 R)-sonnerlactone and (3 r,5 s)-sonnerlactone

Synlett

Volumn , Issue 18, 2011, Pages 2667-2670

  Thirupathi, Barla ^a   Gundapaneni, Raghava R ^a   Mohapatra, Debendra K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

antiproliferative; Jacobsens hydrolytic kinetic resolution; ring closing metathesis; Sharpless asymmetric epoxidation; sonnerlactone

Indexed keywords

2,4,6 TRIHYDROXY BENZOIC ACID; GRISEOFULVIN; LACTONE DERIVATIVE; PROPYLENE OXIDE; SONNERLACTONE; UNCLASSIFIED DRUG; XESTODECALACTONE A; XESTODECALACTONE B; XESTODECALACTONE C;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CHEMICAL BOND; DIHYDROXYLATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS KINETICS; OXIDATION;

EID: 80455176796     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289529     Document Type: Article

References (42)

1. Li K.-K, Lu Y.-J, Song X.-H, She Z.-G, Wu X.-W, An L.-K, Ye C.-X, Lin Y.-C, Bioorg. Med. Chem. Lett. 2010 20 3326
2. Edrada R A., Heubes M, Brauers G, Wray V, Berg A, Gräfe U, Wohlfarth M, Mühlbacher J, Schaumann K, SudarsonoBringmann G, Proksch P, J. Nat. Prod. 2002 65 1598
3. Sponga F, Cavaletti L, Lazzarini A, Borghi A, Ciciliato I, Losi D, Marinelli F, J. Biotechnol. 1999 70 65
4. Huang Z, Cai X, Shao C, She Z, Xia X, Chen Y, Yang J, Zhou S, Lin Y, Phytochemistry 2008 69 1604
5. Bernan V S., Greenstein M, Maiese W M., Adv. Appl. Microbiol. 1997 43 57
6. Fenical W, Jansen P R., Annu. Rev. Microbiol. 1994 48 559
7. Gradillas A, Pérez-Castells J, Angew. Chem. Int. Ed. 2006 45 6086
8. Deiters A, Martin S F., Chem. Rev. 2004 104 2199
9. Grubbs R H., Tetrahedron 2004 60 7117
10. Prunet J, Angew. Chem. Int. Ed. 2003 42 2826
11. Love J A., In Handbook of Metathesis Grubbs R H. Wiley-VCH Weinheim 2003 296
12. Trnka T M., Grubbs R H., Acc. Chem. Res. 2001 34 18
13. Fürstner A, Angew. Chem. Int. Ed. 2000 39 3012
14. Maier M E., Angew. Chem. Int. Ed. 2000 39 2073
15. Grubbs R H., Chang S, Tetrahedron 1998 54 4413
16. Armstrong S K., J. Chem. Soc., Perkin Trans. 1 1998 371
17. Gerlach K, Quitschalle M, Kalesse M, Tetrahedron Lett. 1999 40 3553
18. Nevalainen M, Koskinen A M. P., Angew. Chem. Int. Ed. 2001 40 4060
19. Mohapatra D K., Reddy D P., Dash U, Yadav J S., Tetrahedron Lett. 2011 52 151
20. Mohapatra D K., Somaiah R, Rao M M., Caijo F, Mauduit M, Yadav J S., Synlett 2010 1223
21. Mohapatra D K., Dash U, Naidu P R., Yadav J S., Synlett 2009 2129
22. Mohapatra D K., Sahoo G, Ramesh D K., Sastry G N., Tetrahedron Lett. 2009 50 5636
23. Mohapatra D K., Rahman H, Pal R, Gurjar M K., Synlett 2008 1801
24. Mohapatra D K., Ramesh D K., Giardello M A., Chorghade M S., Gurjar M K., Grubbs R H., Tetrahedron Lett. 2007 48 2621
25. Gurjar M K., Karmakar S, Mohapatra D K., Tetrahedron Lett. 2004 45 4525
26. Gurjar M K., Nagaprasad R, Ramana C V., Karmakar S, Mohapatra D K., ARKIVOC 2005 (iii) 237
27. Mohapatra D K., Yellol G S., ARKIVOC 2005 (iii) 144
28. Mohapatra D K., Durugkar K A., ARKIVOC 2004 (i) 146
29. Mohapatra D K., Yellol G S., ARKIVOC 2003 (ix) 21
30. Nielson L P. C., Stevenson C P., Blackmond D G., Jacobsen E N., J. Am. Chem. Soc. 2004 126 1360
31. Schaus S E., Brandes B D., Larrow J F., Tokunaga M, Hansen K B., Gould A E., Furrow M E., Jacobsen E N., J. Am. Chem. Soc. 2002 124 1307
32. Kumar P, Gupta P, Naidu S V., Chem. Eur. J. 2006 12 1397
33. Yu W, Mei Y, Hua Z, Jin Z, Org. Lett. 2004 6 3217
34. Gao Y, Hanson R M., Klunder J M., Ko S Y., Masamune H, Sharpless K B., J. Am. Chem. Soc. 1987 109 5765
35. Coussens L M., Werb Z, Nature (London) 2002 420 860
36. Rao A V. R., Reddy E R., Joshi B V., Yadav J S., Tetrahedron Lett. 1987 28 6497
37. Mitsunobu O, Synthesis 1981 1
38. Subramanian L R., Hanack M, Chang L W. K., Imhoff M A., Schleyer P, Effenberger F, Kurtz W, Stang P J., Dueber T E., J. Org. Chem. 1976 41 4099
39. Luo F.-T, Wang R.-T, Tetrahedron Lett. 1991 32 7703
40. Dushin R G., Danishefsky S J., J. Am. Chem. Soc. 1992 114 655
41. Kamisuki S, Takashi S, Mizushina Y, Hanashima S, Kuramochi K, Kobayashi S, Sakaguchi K, Nakata T, Sugawara F, Tetrahedron 2004 60 5695
42. Bhattacharjee A, Sequil O R., DeBrabander J K., Tetrahedron Lett. 2000 41 8069