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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.

 

    1. Sha, C.-K.; Jean, T.-S.; Wang, D.-C. Tetrahedron Lett. 1990, 31, 3745.
    2. Sha, C.-K.; Shen, C.-Y.; Jean, T.-S.; Chiu, R.-T.; Tseng, W.-H. Tetrahedron Lett. 1993, 34, 7641.
    3. 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.



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