Zinc mediated deoxygenation of 4-hydroxy-2-butenoic acid moiety. An application for the synthesis of multifunctional chiral synthon

Tetrahedron

Volumn 52, Issue 12, 1996, Pages 4457-4466

  Yadav, J S ^a   Barma, D K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0029983107     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00093-2     Document Type: Article

References (22)

1. (a) Hanessian, S. The total synthesis of natural products, the Chiron approach, Organic Chem. Series. Pargamon Press; Oxford, 1983 ; Vol. 3.
2. (b) Seebach, D.; Vasella, A. Modern Synthetic Methods. Scheffold, R (ed.); Frankfurt; 1980; Vol. 2.
3. (c) Schnurrenberger, P.; Hungerbuhler, E.; Seebach, D. Liebigs Ann. Chem. 1987, 733.
4. Rama Rao, A.V.; Reddy, E.R.; Joshi, B.V.; Yadav, J.S. Tetrahedron Lett. 1987, 28, 6497.
5. Samuelsson, B.; Dahlen, S.; Lindgreen, J.A.; Rouzer, Carol A.; Serhan, Charles N. Science, 1987, 237, 1171.
6. Rokach, J.; Guindon, Y.; Young, R.N.; Adams, J.; Alkinson, J.G. Total Synthesis of Natural Products. Ed. Apsiman, J.; Wiley Inter Science; New York; 1988, 7, 141.
7. Zamboni, R.; Rokach, J. Tetrahedron Lett. 1982, 23, 2631.
8. Zamboni, R.; Rokach, J. Tetrahedron Lett. 1983, 24, 999.
9. Corey, E.J. Prog. Lipid. Res. 1986, 25, 625.
10. Kato, T.; Yamaguchi, Y.; Ohnuma, S.; Uyehara, T.; Namai, T.; Kodama, M.; Shiobara, Y. Chemistry Letters, 1986, 577-588.
11. Kang, S.; Kim, S.G.; Park, D.; Lee, J.; Yoo, W.; Pak, C.S. J.Chem.Soc., Perkin Trans-1. 1993, 9-10.
12. Molander, G.A.; Belle, B.E.L.; Hahn, G. J. Org. Chem. 1986, 51, 5259.
13. (a) Takai, K.; Kakiuchi, T.; Utimota ,K. J.Org. Chem. 1994, 59, 2671.
14. (b) Erdik, E. Tetrahedron.1987, 43, 2203.
15. Horton, D.; Koh, D. Carbohydrate Research. 1993, 250, 231-247.
16. Kagan, H.B.; Namy, J.L.; Girard, P. Tetrahedron Suppl. 1981, 37, 175.
17. Levene, P.A.; Stiller, E.T. J. Biol. Chem. 1933, 102, 187.
18. Ohrui, H.; Jones, Gordon, H.; Moffatt, John G.; Moddox, Michael L.; Christensen, Arild T. and Byram, Susan K. J. Am. Chem.Soc. 1995, 97, 4602-4613.
19. Wolfrom, M.L., Newlin, M.R.: Stahly, E.E. J. Am. Chem. Soc. 1993, 53, 4379.
20. Corey, E.J.; Enckson, B.W. J. Org. Chem. 1971, 36, 3553.
21. Freudenberg, K. and Wolf, A. Ber. 1927, 60, 232.
22. Curtis, E.J.C.; Jones, J.K.N. Can. J. Chem. 1960, 38, 890.