A convenient strategy for the synthesis of β,γ-unsaturated aldehydes and acids. A construction of skipped dienes

Tetrahedron Letters

Volumn 40, Issue 40, 1999, Pages 7179-7183

  Saha, Goutam ^a   Basu, Manas K ^a   Kim, Seongjin ^a   Jung, Young Ju ^a   Adiyaman, Yurdanur ^a   Adiyaman, Mustafa ^b   Powell, William S ^c   FitzGerald, Garret A ^d   Rokach, Joshua ^a  

^a Florida Institute of Technology ^*  (United States)

^b ABANT IZZET BAYSAL UNIVERSITY   (Turkey)

^c MCGILL UNIVERSITY   (Canada)

^d UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

, Unsaturated aldehydes; 5 Oxo ETE; Arachidonic acid; Eicosanoids; Isoprostanes; Pb(OAc)4

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALDEHYDE; ALKADIENE; ARACHIDONIC ACID; ICOSANOID; ISOPROSTANE DERIVATIVE; POLYUNSATURATED FATTY ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033215051     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01498-7     Document Type: Article

References (13)

1. Berhane, K.; Ray, A. A.; Khanapure, S. P.; Rokach, J.; Powell, W. S. J. Biol. Chem. 1998, 273, 20951-20959.
2. Khanapure, S. P.; Powell, W. S.; Rokach, J. J. Org. Chem. 1998, 63, 8976-8982.
3. Rokach, J.; Khanapure, S. P.; Hwang, S. W.; Adiyaman, M.; Lawson, J. A.; FitzGerald, G. A. Prostaglandins 1997, 54, 823-851.
4. Pratico, D.; Tangirala, R. K.; Rader, D. J.; Rokach, J.; FitzGerald, G. A. Nature Med. 1998, 4, 1189-1192.
5. Adiyaman, M.; Jung, Y.; Kim, S.; Saha, G.; Powell, W. S.; FitzGerald, G.; Rokach, J. Tetrahedron Lett. 1999, 40, 4019-4022.
6. 1H NMR of the mixtures of isomers. The aldehydic proton of the desired β,γ-unsaturated compounds appears at δ 9.64-9.67 as a broad triplet and the aldehydic proton of the α,β-unsaturated isomers appears as expected upfield at δ 9.52-9.55 as a doublet. The ratio of these two protons gives an accurate indication of the isomerization process.
7. (a) Bertozzi, S.; Campigli, N.; Vitulli, A.; Lazzaroni, R.; Salvadori, P. J. Organomet. Chem. 1995, 487, 41-45.
8. (b) Horiuchi, T.; Ohta, T.; Nozaki, K.; Takaya, H. Chem. Commun. 1996, 155-156.
9. 3) δ 9.66 (br t, J=1.5 Hz, 1H), 5.70 (m, 1H), 5.54 (m, 1H), 3.19 (d br, J=7.1 Hz, 2H), 2.03 (q, J=7.16 Hz, 2H), 1.29 (m, 6H), 0.89 (t, J=6.92 Hz, 3H).
10. Rokach, J.; Khanapure, S. P.; Hwang, S. W.; Adiyaman, M.; Lawson, J. A.; FitzGerald, G. A. Prostaglandins 1997, 54, 853-873.
11. Rokach, J.; Khanapure, S. P.; Hwang, S. W.; Adiyaman, M.; Schio, L.; FitzGerald, G. A. Synthesis, First Special Issue, Natural Products Synthesis 1998, 569-580.
12. Adams, J.; Rokach, J. Tetrahedron Lett. 1984, 25, 35-38.
13. Viala, J.; Santelli, M. J. Org. Chem. 1988, 53, 6121-6123.