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Asymmetric Total Synthesis of Nakadomarin A Li Nan 2013.7.6.

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Presentation on theme: "Asymmetric Total Synthesis of Nakadomarin A Li Nan 2013.7.6."— Presentation transcript:

1 Asymmetric Total Synthesis of Nakadomarin A Li Nan

2 Nakadomarin A 是日本科学家 Kobayashi 于 1997 年从日本冲绳县 (Okinawa) 庆良间列岛 (Kerama Islands) 的一种海绵 Amphimedon sp.(SS-264) 中分离得到了一种新型 Manzamine 类海洋生物碱。它具有完全环 状结构 6/5/5/5/8/15 六环体系, 其中一个环为 呋喃环, 并具有一定的生理活性。 Nishida, A. Angew. Chem. 2004, 116, Kerr, M. A. J. Am. Chem. Soc. 2007, 129, Dixon, D. J. J. Am. Chem. Soc. 2009, 131, Evans, D. A. J. Am. Chem. Soc. ASAP 2

3 Nishada’s Asymmetric Total Synthesis of (-)-Nakadomarin A 3

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8 Kerr’s Asymmetric Total Synthesis of (+)-Nakadomarin A 8

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12 Dixon’s Asymmetric Total Synthesis of (-)-Nakadomarin A 12

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16 Evans’s Asymmetric Total Synthesis of (-)-Nakadomarin A 16

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19 Matsumoto, M. Tetrahedron Lett. 1976, 17, Rose bengal 19

20 Peterson, D. J. J. Org. Chem. 1968, 33, 780 Peterson Reaction

21 Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023.

22 Kocienski Synlett 1998, 26 Aissa, C. J. Org. Chem. 2006, 71, 360. Julia-Kocienski Reaction

23 Ono, N. Tetrahedron Lett. 1981, 22, Fu, G. C. J. Org. Chem. 1998, 63, 5296.

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