Stereospecific Total Synthesis of a “Slow Reacting Substance” of Anaphylaxis, Leukotriene C-

Journal of the American Chemical Society

Volumn 102, Issue 4, 1980, Pages 1436-1439

  Corey, E J ^a   Clark, David A ^a   Goto, Giichi ^a   Marfat, Anthony ^a   Mioskowski, Charles ^a   Samuelsson, Bengt ^b   Hammarstrom, Sven ^b  

^a HARVARD UNIVERSITY   (United States)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

LEUKOTRIENE;

DRUG SYNTHESIS; EDITORIAL; STEREOSPECIFICITY;

EID: 0018886731     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00524a045     Document Type: Letter

References (24)

1. Feldberg, W.; Kellaway, C. H. J. Physiol. (London) 1938, 94, 187.
2. Murphy, R. C.; Hammarstrbm, S.; Samuelsson, B. Proc. Natl. Acad. Scl. U.S.A. 1979, 76, 4275.
3. Samuelsson, B.; Borgeat, P.; Hammarstrom, S.; Murphy, R. C. Prostaglandins 1979, 17, 785.
4. Hammarstrom, S.; Murphy, R. C.; Samuelsson, B.; Clark, D. A.; Mioskowski, C.; Corey, E. J. Blochem. Biophys. Res. Commun. 1979, 91, 1266.
5. Hammarstrom, S.; Samuelsson, B.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Corey, E. J. Blochem. Biophys. Res. Commun., in press.
6. For reviews on the biological aspects of SRS see: (a) Parker, C. W. J. Allergy Clin. Immunol. 1979, 63, 1.
7. Orange, R. P.; Austen, K. F. Adv. Immunol. 1969, 10, 105.
8. Orange, R. P.; Murphy, R. O.; Karnovsky, M. L.; Austen, K. P., J. Immunol. 1973, 110, 760.
9. Orange, R. P.; Murphy, R. O.; Austen, K. F. J. Immunol. 1974, 113, 316.
10. Corey, E. J.; Arai, Y.; Mioskowski, C. J. Am. Chem. Soc. 1979, 101, 6748.
11. Ness, R. K.: Diehl, H. W.; Fletcher, H. G., Jr. J. Am. Chem. Soc. 1954, 76, 763.
12. Isler; O.; Gutmann, H.; Montavon, M.; Ruegg, R.; Ryser, G.; Zeller, P. Heiv. Chim. Acta 1957, 40, 1242.
13. Buchanan, J. G.; Edgar, A. R.; Power, M. J.; Theaker, P. D. Carbohydr. Res. 1974, 38, C22.
14. All Revalues given herein were obtained using thin layer chromatography on silica gel plates.
15. Infrared, proton magnetic resonance, and mass spectral (and where appropriate ultraviolet spectral) data were obtained using purified, chroma-tographically homogeneous samples of each synthetic intermediate, and were in agreement with the assigned structure.
16. For preparation see Elphimoff-Felkin, I.; Sarda, P. Tetrahedron Lett. 1972, 725.
17. Collins, J. C.; Hess, W. W.; Frank, F. J. Tetrahedron Lett. 1968, 3363.
18. Wollenberg, R. H. Tetrahedron Lett., 1978, 717. We are indebted to Dr. Wollenberg for a sample and spectra of the precursor reagent, 1-tributyl-stannyl-4-ethoxybutadiene.
19. Corey, E. J.; Enders, D.; Bock, M. G. Tetrahedron Lett. 1976, 7.
20. Because of the instability of the tetraene epoxides 2 and 14 under acidic conditions, silica gel must be deactivated by trlethylamlne before chro-matography. Since these compounds are also air sensitive,5 they were stored under argon in frozen benzene containing 4-hydroxy-2,2,6,6-te-tramethyipiperidinooxy tree radical as antioxidant.
21. In contrast four stereoisomeric products were obtained (as expected) by reaction of W-trifluoroacetylglutathlone methyl ester with the mixture of 5,6-cis and 5,6-trans isomers of (±)-2 synthesized as described earlier;5 these were readily separated by HPLC with one component corresponding to the product from (—)-2.
22. Hydrolysis of the mixture of stereoisomeric27 W-trifluoroacetyl trimethyl esters afforded a mixture of 1 and 3 stereoisomers which was readily resolved by reversed-phase HPLC.
23. Superimposible lines were obtained in extensive dose-response studies using synthetic 1 and leukotriene C-1 with guinea pig ileum as test tissue.
24. Reversed-phase HPLC retention times were in the order cys analogue cys gly analogue 1, as expected.