Diastereoselective schenck ene reaction of singlet oxygen with chiral allylic alcohols; access to enantiomerically enriched 1,2,4-trioxanes

Tetrahedron

Volumn 65, Issue 41, 2009, Pages 8531-8537

  Sabbani, Sunil ^a,b   La Pensée, Louise ^b   Bacsa, John ^b   Hedenström, Erik ^a   O'Neill, Paul M ^b  

^a MID SWEDEN UNIVERSITY   (Sweden)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Allylic alcohols; Antimalarial; Chiral trioxanes; Endoperoxides; Hydroperoxides; MIB

Indexed keywords

1,2,4 TRIOXANE DERIVATIVE; ALLYL ALCOHOL; ANTIMALARIAL AGENT; BETA HYDROPEROXYALCOHOL DERIVATIVE; KETONE DERIVATIVE; REAGENT; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; NONHUMAN; PHOTOOXIDATION; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 69549096060     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.020     Document Type: Article

References (32)

1. Price R.N., Dorsey G., Ashley E.A., Barnes K.I., Baird J.K., d'Alessandro U., Guerin P.J., Laufer M.K., Naidoo I., Nosten F., Olliaro P., Plowe C.V., Ringwald P., Sibley C.H., Stepniewska K., and White N.J. Malar. J. 6 (2007) 1
2. Sriram D., Rao V.S., Chandrasekhar K.V.G., and Yogeeswari P. Nat. Prod. Res. 18 (2004) 503
3. WHO. http://www.who.int/malaria/docs/TreatmentGuidelines2006.pdf.
4. Klayman D.L. Science 228 (1985) 1049
5. Jefford C.W. Drug Discovery Today 12 (2007) 487
6. Butler A.R., Gilbert B.C., Hulme P., Irvine L.R., Renton L., and Whitwood A.C. Free Radical Res. 28 (1998) 471
7. Eckstein-Ludwig U., Webb R.J., van Goethem I.D.A., East J.M., Lee A.G., Kimura M., O'Neill P.M., Bray P.G., Ward S.A., and Krishna S. Nature 424 (2003) 957
8. Krishna S., Uhlemann A.C., and Haynes R.K. Drug Resist. Updates 7 (2004) 233
9. Haynes R.K., Chan W.C., Lung C.M., Uhlemann A.C., Eckstein U., Taramelli D., Parapini S., Monti D., and Krishna S. ChemMedChem. 2 (2007) 1480
10. O'Neill P.M., Miller A., Bickley J.F., Scheinmann F., Chang H.O., and Posner G.H. Tetrahedron Lett. 40 (1999) 9133
11. O'Neill P.M., Rawe S.L., Borstnik K., Miller A., Ward S.A., Bray P.G., Davies J., Oh C.H., and Posner G.H. ChemBioChem. 6 (2005) 2048
12. Griesbeck A.G., El-Idreesy T.T., Fiege M., and Brun R. Org. Lett. 4 (2002) 4193
13. Griesbeck A.G., El-Idreesy T.T., Hoinck L.O., Lex J., and Brun R. Bioorg. Med. Chem. Lett. 15 (2005) 595
14. Griesbeck A.G., Bartoschek A., Ei-Idreesy T.T., Hoinck O., and Miara C. J. Mol. Catal. A: Chem. 251 (2006) 41
15. Lurain A.E., Maestri A., Kelly A.R., Carroll P.J., and Walsh P.J. J. Am. Chem. Soc. 126 (2004) 13608
16. Nugent W.A. Chem. Commun. (1999) 1369
17. Young K., Chen S.-J.J., Walsh P.J., and Nugent W.A. Org. Synth. 82 (2005) 87
18. Schenck G.O. Naturwissenschaften 35 (1948) 28
19. Adam W., and Nestler B. J. Am. Chem. Soc. 115 (1993) 5041
20. Griesbeck A.G., El-Idreesy T.T., and Bartoschek A. Pure Appl. Chem. 77 (2005) 1059
21. Prein M., and Adam W. Angew. Chem., Int. Ed. 35 (1996) 477
22. Nardello V., Caron L., Aubry J.M., Bouttemy S., Wirth T., Chantu R.S.M., and Adam W. J. Am. Chem. Soc. 126 (2004) 10692
23. Adam W., Renze J., and Wirth T. J. Org. Chem. 63 (1998) 226
24. Griesbeck A.G., El-Idreesy T.T., and Bartoschek A. Adv. Synth. Catal. 346 (2004) 245
25. Griesbeck A.G., El-Idreesy T.T., and Lex J. Tetrahedron 62 (2006) 10615
26. Adam W., and Nestler B. J. Am. Chem. Soc. 114 (1992) 6549
27. Clennan E.L., Zhang D., and Singleton J. Photochem. Photobiol. 82 (2006) 1226
28. Bartoschek A., El-Idreesy T., Griesbeck A.G., Hoinck L.O., Lex J., Miara C., and Neudorfl J.M. Synthesis (2005) 2433
29. Singh C. Tetrahedron Lett. 31 (1990) 6901
30. O'Neill P.M., Hindley S., Pugh M.D., Davies J., Bray P.G., Park B.K., Kapu D.S., Ward S.A., and Stocks P.A. Tetrahedron Lett. 44 (2003) 8135
31. Tang Y.Q., Dong Y.X., Wang X.F., Sriraghavan K., Wood J.K., and Vennerstrom J.L. J. Org. Chem. 70 (2005) 5103
32. Yadav J.S., Mysorekar S.V., and Rao A.V.R. Tetrahedron 45 (1989) 7353