First total synthesis of the E type I phytoprostanes

Tetrahedron Letters

Volumn 44, Issue 40, 2003, Pages 7411-7415

  Rodríguez, Ana R ^a   Spur, Bernd W ^a  

^a UMDNJ School of Osteopathic Medicine   (United States)

Author keywords

Enzyme reactions; Hydrolytic kinetic resolution; Phytoprostanes; Protonation; Takai reaction

Indexed keywords

1,2 EPOXYBUTANE; ALKANE DERIVATIVE; AZELAIC ACID; BUTANE; EPOXIDE; ESTER DERIVATIVE; FURAN; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONJUGATION; CYCLOADDITION; DIASTEREOISOMER; HYDROLYSIS; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0042260801     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.08.042     Document Type: Article

References (33)

1. Morrow J.D., Hill K.E., Burk R.F., Nammour T.M., Badr K.F., Roberts L.J. II. Proc. Natl. Acad. Sci. USA. 87:1990;9383-9387.
2. Morrow J.D., Awad J.A., Boss H.J., Blair I.A., Roberts L.J. II. Proc. Natl. Acad. Sci. USA. 89:1992;10721-10725.
3. Taber D.F., Morrow J.D., Roberts L.J. II. Prostaglandins. 53:1997;63-67.
4. Rokach J., Khanapure S.P., Hwang S.-W., Adiyaman M., Lawson J.A., FitzGerald G.A. Prostaglandins. 54:1997;853-873.
5. Rokach J., Khanapure S.P., Hwang S.-W., Adiyaman M., Schio L., FitzGerald G.A. Synthesis. 1998;569-580.
6. Schrader T.O., Snapper M.L. J. Am. Chem. Soc. 124:2002;10998-11000.
7. Quan L.G., Cha J.K. J. Am. Chem. Soc. 124:2002;12424-12425.
8. Taber D.F., Xu M., Hartnett J.C. J. Am. Chem. Soc. 124:2002;13121-13126.
9. Zanoni G., Porta A., Vidari G. J. Org. Chem. 67:2002;4346-4351.
10. Zanoni G., Porta A., Castronovo F., Vidari G. J. Org. Chem. 68:2003;6005-6010.
11. Parchmann S., Mueller M.J. J. Biol. Chem. 273:1998;32650-32655.
12. Roberts L.J. II, Montine T.J., Markesbery W.R., Tapper A.R., Hardy P., Chentob S., Dettbarn W.D., Morrow J.D. J. Biol. Chem. 273:1998;13605-13612.
13. Mueller M.J. Chem. Biol. 5:1998;323-333.
14. Imbusch R., Mueller M.J. Plant. Physiol. 124:2000;1293-1303.
15. Imbusch R., Mueller M.J. Free Radic. Biol. Med. 28:2000;720-726.
16. Fangour S.E., Guy A., Vidal J.-P., Rossi J.-C., Durand T. Tetrahedron Lett. 44:2003;2105-2108.
17. Krischke M., Loeffler C., Mueller M.J. Phytochemistry. 62:2003;351-358.
18. Sih C.J., Price P., Sood R., Salomon R.G., Peruzzotti G., Casey M. J. Am. Chem. Soc. 94:1972;3643-3644.
19. Rodríguez A.R., Spur B.W. Tetrahedron Lett. 43:2002;4575-4579.
20. Rodríguez A.R., Spur B.W. Tetrahedron Lett. 43:2002;9249-9253.
21. D'Auria M. Heterocycles. 52:2000;185-194.
22. Rodríguez A., Nomen M., Spur B.W., Godfroid J.J. Eur. J. Org. Chem. 1999;2655-2662. and references cited therein.
23. abstract
24. 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. 124:2002;1307-1315.
25. Rodríguez A., Nomen M., Spur B.W., Godfroid J.J., Lee T.H. Tetrahedron. 57:2001;25-38.
26. Rodríguez A., Nomen M., Spur B.W., Godfroid J.J. Tetrahedron Lett. 40:1999;5161-5164.
27. Takai K., Nitta K., Utimoto K. J. Am. Chem. Soc. 108:1986;7408-7410.
28. Evans D.A., Black W.C. J. Am. Chem. Soc. 115:1993;4497-4513.
29. Fürstner A. Chem. Rev. 99:1999;991-1045.
30. The enantiomeric excess was determined by Chiral-HPLC [column: Chiracel OD, mobile phase: hexane/i-PrOH (96:4) λ=210 nm].
31. Babiak K.A., Ng J.S., Dygos J.H., Weyker C.L., Wang Y.-F., Wong C.-H. J. Org. Chem. 55:1990;3377-3381.
32. The ratios were determined by HPLC [column: Nucleosil 100 Silica 5 μm, mobile phase: hexane/i-PrOH (99.6:0.4) λ=210 nm].
33. 4 and evaporating afforded crude 2 that was purified by flash chromatography [silica gel, EtOAc] affording 27.2 mg (81%) of 2.