Stereoselective first total synthesis, confirmation of the absolute configuration and bioevaluation of botryolide-E

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 3, 2011, Pages 997-1000

  Reddy, D Kumar ^a   Shekhar, V ^a   Prabhakar, P ^a   Babu, D Chanti ^a   Ramesh, D ^a   Siddhardha, B ^a   Murthy, U S N ^a   Venkateswarlu, Y ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Lactone; Antimicrobial; Botryolide E; Jacobsen's hydrolytic kinetic resolution (HKR); Sharpless asymmetric dihydroxylation; Staphylococcus aureus

Indexed keywords

BOTRYOLIDE E; CLOTRIMAZOLE; EPOXIDE; NATURAL PRODUCT; NITROFURANTOIN; PENICILLIN G; PROPYLENE OXIDE; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BACILLUS SUBTILIS; CANDIDA ALBICANS; CONTROLLED STUDY; DEPROTECTION REACTION; DIHYDROXYLATION; DRUG POTENCY; DRUG SCREENING; ESCHERICHIA COLI; HYDROLYSIS; LACTONIZATION; NONHUMAN; ONE POT SYNTHESIS; RHIZOPUS ORYZAE; RING OPENING; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; STEREOCHEMISTRY;

4-BUTYROLACTONE; ACETATES; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACILLUS SUBTILIS; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM;

BACILLUS SUBTILIS; ESCHERICHIA COLI; FUNGI; STAPHYLOCOCCUS AUREUS;

EID: 78751641643     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.12.024     Document Type: Article

References (20)

1. R.M. Klevens, M.A. Morrison, J. Nadle, S. Petit, K. Gershman, S. Ray, L.H. Harrison, R. Lynfield, G. Dumyati, J.M. Townes, A.S. Craig, E.R. Zell, G.E. Fosheim, L.K. McDougal, R.B. Carey, and S.K. Fridkin J. Am. Med. Assoc. 298 2007 1763
2. S.B. Levy, and B. Marshall Nat. Med. 10 2004 S122
3. A. Tomasz N. Eng. J. Med. 330 1994 1247
4. S.K. Fridkin, J.R. Edwards, J.M. Courval, H. Hill, F.C. Tenover, R. Lawton, R.P. Gaynes, and J.E. McGowan Jr. Ann. Int. Med. 135 2001 175
5. H.M.R. Hoffmann, and J. Rabe Angew. Chem., Int. Ed. Engl. 24 1985 94
6. D.H. Li, T.J. Zhu, H.B. Liu, C.Y. Fang, Q.Q. Gu, and W.M. Zhu Arch. Pharmacol. Res. 29 2006 624
7. F. Cateni, J. Zilic, M. Zacchigna, P. Bonivento, F. Frausin, and V. Scarcia Eur. J. Med. Chem. 41 2006 192
8. S. Ma, Z. Shi, and Z. Yu Tetrahedron 55 1999 12137
9. A.A. Sy, D.C. Swenson, J.B. Gloer, and D.T. Wicklow J. Nat. Prod. 71 2008 415
10. D. Kumar Reddy, V. Shekhar, T. Srikanth Reddy, S. Purushotham Reddy, and Y. Venkateswarlu Tetrahedron: Asymmetry 20 2009 2315
11. V. Shekhar, D. Kumar Reddy, V. Suresh, D. Chanti Babu, and Y. Venkateswarlu Tetrahedron Lett. 51 2010 946
12. P. Prabhakar, S. Rajaram, D. Kumar Reddy, V. Shekar, and Y. Venkateswarlu Tetrahedron: Asymmetry 21 2010 216
13. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307
14. J.S. Yadav, P.M.K. Reddy, M.K. Gupta, and C.J. Chary Synthesis 23 2007 3639
15. H.C. Kolb, and K.B. Sharpless Chem. Rev. 94 1994 2483
16. National Committee for Clinical Laboratory Standards (NCCLS), Standard Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Which Grows Aerobically; Nat. Comm Clini. Lab. Stands: Villanova, 1982, p 242.
17. D. Kumar Reddy, V. Shekhar, P. Prabhakar, B. Chinna Babu, B. Siddhardha, U.S.N. Murthy, and Y. Venkateswarlu Eur. J. Med. Chem. 45 2010 4657
18. E. Margery Linday, Practical Introduction to Microbiology; E. & F.N. Spon: UK, 1962, p 177.
19. Ref. 13b.
20. +.