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Pure Appl. Chem., Vol. 70, No. 11,
pp.2138, 1998
a-Carbonyl
radical cyclization: Application toward total syntheses of natural products*
Chin-Kang Sha*, Shih-Jung Huang, Rei-Torng Chiu,
Shinn-Horng Lih, Cheng-Tso Tseng, K. C. Santhosh, Ching-Jung Chang,
An-Wei Hong, Pyng-Chang Cherng, Wei-Hong Tseng, Wen-Yueh Ho, Fu-Shing
Wang, and Tzung-Huei Jeng
Department of Chemistry, National Tsing Hua University, Hsinchu 300,
Taiwan, R. O. C.
E-mail: [email protected]
Abstract: Intramolecular radical cyclization reactions have now
been used routinely to synthesize spiro and fused carbocyclic and heterocyclic
structures. We recently reported that a
-carbonyl radicals 1, generated from the corresponding iodo compounds,
underwent intramolecular radical cyclization smoothly to afford products
2.1, 2
Application of these intramolecular radical cyclization reactions to
the total syntheses of (-)-dendrobine (3),3 (-)-5-oxosilphiperfol-6-ene
(4) and paniculatine (5) will be presented.
- Sha, C.-K.; Jean, T.-S.; Wang, D.-C. Tetrahedron
Lett. 1990, 31, 3745.
- Sha, C.-K.; Shen, C.-Y.; Jean, T.-S.; Chiu, R.-T.;
Tseng, W.-H. Tetrahedron Lett. 1993, 34, 7641.
- Sha, C.-K.; Chiu, R.-T.; Yang, C.-F.; Yao, N.-T.;
Tseng, W.-H.; Liao, F.-L.;Wang S.-L. J. Am. Chem. Soc. 1997,
119, 4130.
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* Invited lecture presented at the International
Conference on Bioversity and Bioresources: Conservation and Utilization,
23-37 November 1997, Phuket, Thailand.
Page last modified 19 April 1999.
Copyright ©1997, 98, 99 International Union of Pure and Applied
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