利用[3+3]環合加成反應可以建構出不對稱環戊亞醯胺，經位置選擇性還原反應後可得到羥基內醯胺與內醯胺，再將其應用到多取代吡啶-2-酮、塔卡莫寧與迪普蘭群的合成研究。

A convenient method for the preparation of hydroxyl lactams via regioselective reduction of N-alkyl-3-sulfonyl glutarimides is described. The useful building block is applied to synthesize polysubstituted pyridin-2-one, tacamonine and deplancheine.

第一篇：多取代吡啶-2-酮的合成研究
第一章：3-磺酸基-5-取代環戊醯亞胺的合成與位置選擇性還原反應的探討
第二章：3,5-雙取代吡啶-2-酮與天然物塔卡莫寧的合成研究
第三章：5-羥基-6-取代內醯胺與5-羥基吡啶-2-酮的合成研究
第二篇：迪普蘭群的全合成

1. a) Strunz, G. M.; Findlay, J. A. The Alkaloids; Brossi, A., Ed.; Academic: New York, 1985; Vol. 26, pp. 89; b) Aguinaldo, A. M.; Read, R. W. Phytochemistry 1990, 29, 2309; c) Bolzani, V. das.; Gunatilaka, A. A.L.; Kingston, D. G. I. Tetrahedron 1995, 51, 5929; d) Astudillo, S. L.; Jurgens, S. K.; Schmeda Hirschmann, G.; Griffith, G. A.; Holt, D. H.; Jenkins, P. R. Planta Med 1999, 65, 161; e) Evans, S. V.; Fellows, L. E.; Shing, T. K. M.; Fleet, G. W. J. Phytochemistry 1985, 24. 1953; f) Daly, J. W.; Garrafo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; San Diego, CA: Academic Press, 1993; pp. 85; g) Oefner, C.; Binggeli, A.Breu, V.; Bur, D.; Clozel, J. P.; D’arcy, A.; Dorn, A.; Fichli, W.; Gruninger, F.; Guller, R.; Hirth, G.; Marki, H.; Wostl, W. Chem. Biol. 1999, 6, 127.
2. Reviews: (a) Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023; (b) Daly, J. W.; Spande, T. F. In Alkaloids : Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4, Chapter 1, pp. 1–274.
3. For a recent review, see: (a) Saxton, J. E. In The Alkaloids; Cordell, G. A., Ed.; Academic: New York, 1998; Vol. 51, pp 1-197. For syntheses of aspidospermidine, see: Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521 and references cited therein.
4. (a) Roth, E.; Altman, J.; Kapon, M.; Ben-Ishai, D. Tetrahedron 1995, 51, 801; (b) Manteca, I.; Sotomayor, N.; Villa, M.-J.; Lete, E. Tetrahedron Lett. 1996, 37, 7841; (c) Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914; (d) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661; (e) Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. Tetrahedron Lett. 1999, 40, 2169.
5. (a) Metais, E.; Overman, L. E.; Rodriguez, M. I.; Stearns, B. A. J. Org. Chem. 1997, 62, 9210; (b) Padwa, A.; Henning, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144; (c) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C. Tetrahedron: Asymmetry 1998, 9, 4361.
6. (a) Ollero, L.;Mentink, G.; Rutjes, F. P. J. T.; Speckamp,W. N.; Hiemstra, H. Org. Lett. 1999, 1, 1331; (b) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367; (c) Beyersbergen van Henegouwen,W.G.; Fieseler, R. M.; Rutjes, F. P. J. T.; Hiemstra, H. Angew. Chem., Int. Ed. 1999, 38, 2214.
7. Chang, M. Y.; Chang, B. R.; Tai, H. M.; Chang, N. C. Tetrahedron Lett. 2000, 41, 10273.