Enantiopure N-Acyldihydropyridones as Synthetic Intermediates:  Asymmetric Syntheses of Indolizidine Alkaloids (−)-205A, (−)-207A, and (−)-235B

Author:

Comins Daniel L.1,LaMunyon Donald H.1,Chen Xinghai1

Affiliation:

1. Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Reference32 articles.

1. Reviews:  (a) Suffness, M.; Cordell, G. A. InThe Alkaloids; Brossi, A., Ed.; Academic Press:  Orlando, FL, 1985; Vol. 25, Chapter 1, pp 3−355. (b) Gellert, E. InAlkaloids:  Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons:  New York, 1987; Vol. 5, p 55. (c) Takahata, H.; Momose, T. InThe Alkaloids; Cordell, G. A., Ed.; Academic Press, Inc.  San Diego, 1993; Vol. 44, Chapter 3. (d) Michael, J. P.Nat. Prod. Rep.1997,14, 21−41.

2. For recent examples of and leading references to the synthesis of indolizidine natural products see:  (a) Angle, S. R.; Breitenbucher, J. G. InStudies in Natural Products Chemistry; Stereoselective Synthesis, Atta-ur-Rahman, Ed.; Elsevier:  New York, 1995; Vol. 16, Part J, pp 453−502. (b) Okano, T.; Sakaida, T.; Eguchi, S.Heterocycles1997,44, 227−236. (c) Comins, D. L.; Zhang, Y. M.J. Am. Chem. Soc.1996,118, 12248−12249. (d) Michael, J. P.; Gravestock, D.Synlett1996, 981−982. (e) Thanh, G. V.; Célérier, J. P.; L'hommet, G.Tetrahedron Asymmetry1996,7, 2211−2212. (f) Chan, C.; Cocker, J. D.; Davies, H. G.; Gore, A.; Green, R. H.Bioorg. Med.Chem. Lett.1996,6, 161−164. (g) Li, Y. W.; Marks, T. J.J. Am. Chem. Soc.1996,118, 707−708. (h) Takahata, H.; Bandoh, H.; Momose, T.Heterocycles1996,42, 39−42.

3. (a) Comins, D. L.; Joseph, S. P. InAdvances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: Inc.  Greenwich, CT, 1996; Vol. 2, pp 251−294.

4. Regiospecific substitution of N-acyl-2,3-dihydro-4-pyridones at C-5 via halogenation and cross-coupling

5. Preparation of 2,6-disubstituted 2,3-Dihydro-4-pyridones: Dehydrogenation of trimethylsilyl enol ethers with palladium (ii) acetate

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