Halolactonization reaction using N-haloimides

Author:

Cook Chae-ho,Cho Youn-sang,Jew Sang-sup,Suh Young-guh,Kang Eung-ku

Publisher

Springer Science and Business Media LLC

Subject

Organic Chemistry,Drug Discovery,Molecular Medicine

Reference25 articles.

1. Parts of the present results have appeared in three preliminary communications. a) Cook, C., Cho, Y., Jew, S., and Suh, Y.: Studies On novel halolactonization using N-haloimides under non-aqueous media(I). Bromolactonization reaction.Seoul Uni. J. Pharm. Sci.,4, 109 (1979). b) Cook, C. and Kang, E., Novel bromolactonization using N-bromophthalimide.Arch. Pharm. Res.,4, 137 (1981). c) Jew, S., Novel aspects of bromolactonization reaction using N-haloimides in an aprotic polar solvent.ibid. Arch. Pharm. Res.,5, 97 (1982).

2. These results were taken in part from the M.S., theses of a) Suh, Y.: Studies on novel halocyclization using N-haloimides, Seoul National University Seoul (1980). b) Kang E.: Studies on novel halobactonization.ibid. Seoul National University Seoul (1981).

3. House, H.O.:Mordern Synthetic Reactions, 2nd ed., W.A. Benjamin, Inc., Meleno Park, California 441, p. (1972).

4. Wenkert, E., Liu, L.H., and Johnston, D.B.R.; Approach to ring E of reserpinoid substances.J. Org. Chem.,30, 722(1965). b) Still, W.C., and Schneider, M.J.: Convergent route to α-substituted acrlic esters and application to the the total synthesis of (±)-frullanolide.J. Am. Chem. Soc.,99, 948(1977). c) Danishefsky, S., Schuda, P.I., Kitahara, T., and Etheredge, S.J.: Total synthesis of dl-vernolepin and dl-vernomenin.ibid. J. Am. Chem. Soc.,99, 6066(1977).

5. Corey, E.J., Schaaf, T.K., Huber, W., Koelliker, U., Weinshenker, N.M.: Total synthesis of prostaglandins F2α and E2 as the naturally occuring forms.J. Am. Chem. Soc.,92, 397 (1970). b) Corey, E.J., Trybulski, E.J., Melvin, Jr. L.J., Lett, R., Sheldrake, P.W., Falck, J.R., Brunelle, D.J., Haslanger, M.F., Kim, S.: Total synthesis of erythromycins. 3. Stereoselective route to intermediates, corresponding to C(1) to (9) and C(10) to (13) fragments of erythronolide B.J. Am. Chem. Soc.,100, 4618(1978). c) Corey, E.J., and Hase, T.: Studies on the total synthesis of rifamycin. Highly stereoselective synthesis of intermediates for construction of the C(15) to C(29) chain.Tetra. Lett.,1979, 335. d) Corey, E.J., Niwa, H., and Falck, J.F.: Selective epoxidation of eicosa-cis-5,8,11,14-tetraenoic (arachidonic) acid and eicosa-cis-8, 11,4-trienoic acid.J. Am. Chem. Soc.,101, 1586 (1979).

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