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Total Synthesis of Rollicosin. Cheng-Lin Lee b , Ming-Jung Wu a * a Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan. b Graduate Institute of Pharmaceutical Sciences, Kaohsiung Medical University, Kaohsiung, Taiwan.
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Total Synthesis of Rollicosin Cheng-Lin Leeb, Ming-Jung Wu a* a Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, Taiwan. b Graduate Institute of Pharmaceutical Sciences, Kaohsiung Medical University, Kaohsiung, Taiwan. Tel: 886-7-3121101 ext 2220; Fax: 886-7-3125339; E-mail: mijuwu@cc.kmu.edu.tw Abstract: Scheme 5. Synthesis of 2 Rollicosin 11, isolated by Wu et al. from annonaceae plant, Rollina mucosa Baill, exhibited potent cytotoxicities against many human cancer lines. Recently, we have successfully synthesized the Squamstolide 22a, b based on a palladium catalyzed reaction. According to this discovery rollicosin was synthesized by the same coupling reaction of iodoacetylene 3 and terminal acetylene 4. All these efforts of the syntheses of rollicosin and its analog 26 are described herein. Scheme 3. Synthesis of 2 Figure 1. Structures of 1 and 2 Figure 2. Retrosynthetic analysis of 1 Scheme 1. Synthesis of 3 Scheme 4. Synthesis of 26 Ref: (1) Liaw, C. C.; Chang, F. R.; Wu, M. J.; Wu, Y. C. J. Nat. Prod. 2003, 66, 279. (2) (a) Xie, H. H.; Wei, X. Y.; Wang, J. D.; Liu, M. F.; Yang, R. Z. Chin. Chem. Lett. 2003, 14, 588. (b) Lee, C. L.; Lin, C. F.; Lin, W. R.; Wang, K. S.; Chang, Y. H.; Lin, S. R.; Wu, Y. C.; Wu, M. J. Bioorg. Med. Chem. 2005, 13, 5864.
