In situ alcohol oxidation - Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: Application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid

Tetrahedron Letters

Volumn 44, Issue 1, 2003, Pages 115-118

  Blackburn, Leonie ^a   Kanno, Hisashi ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

5 OXOEICOSATETRAENOIC ACID; ACETAMIDE DERIVATIVE; ALLYL ALCOHOL; AMIDE; ARACHIDONIC ACID; BENZYL ALCOHOL; MANGANESE DIOXIDE; N METHOXY N METHYL 2 (TRIPHENYLPHOSPHORANYLIDINE)ACETAMIDE; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; ELECTRON; GEOMETRY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; WITTIG REACTION;

EID: 0037212996     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02498-X     Document Type: Article

References (16)

1. Wei X., Taylor R.J.K. Tetrahedron Lett. 39:1998;3815-3818.
2. Wei X., Taylor R.J.K. J. Org. Chem. 65:2000;616-620.
3. Blackburn L., Wei X., Taylor R.J.K. Chem. Commun. 1999;1337-1338.
4. Outram H.S., Raw S.A., Taylor R.J.K. Tetrahedron Lett. 43:2002;6185-6187.
5. Blackburn L., Pei C., Taylor R.J.K. Synlett. 2002;215-218.
6. Evans D.A., Kaldor S.W., Jones T.K., Clady J., Stout T.J. J. Am. Chem. Soc. 112:1990;7001-7031.
7. Novel products were fully characterised; known products gave consistent spectroscopic data.
8. 2 (Aldrich, 21764-6; 10 mmol) and the reaction was stirred at the specified temperature. After the specified time, the mixture was filtered through Celite® washing with dichloromethane, and the volatiles removed in vacuo. The products were then purified by column chromatography.
9. As well as the 1,2-addition product (76%), the 1,4-adduct was also obtained (14%).
10. Powell W.S., Gravel S., Halwani F., Hii C.S., Huang Z.H., Tan A.M., Ferrante A. J. Immunol. 159:1997;2952-2959. and references cited therein.
11. Mohapatra S., Capdevila J.H., Murphy R.C., Hevko J.M., Falck J.R. Tetrahedron Lett. 42:2001;4109-4110.
12. Khanapure S.P., Saha G., Sivendran S., Powell W.S., Rokach J. Tetrahedron Lett. 41:2000;5653-5657.
13. Khanapure S.P., Shi X.-X.S., Powell W.S., Rokach J. J. Org. Chem. 63:1998;337-342.
14. Kerdesky F.A.J., Schmidt S.P., Holms J.H., Dyer R.D., Carter G.W. Tetrahedron Lett. 26:1985;2143-2146.
15. see also Lapitskaya M.A., Vasilijeva L.L., Pivnitsky K.K. Synthesis. 1993;65-66.
16. Yadav J.S., Bhanu L.R.M., Dutta D. Tetrahedron. 54:1998;3929-3934.