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Enantioselective Total Synthesis of Ecteinascidin 743

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Presentation on theme: "Enantioselective Total Synthesis of Ecteinascidin 743"— Presentation transcript:

1 Enantioselective Total Synthesis of Ecteinascidin 743
Nan Li

2 Ecteinascidin 743, a tetrahydroisoquinoline alkaloid, was isolated from the Caribbean tunicate Ecteinascidia turbinata by Rinehart and co-workers. This alkaloid attracted strong interest as a potential anticancer agent because of its combination of strong cytostatic properties and antitumor activity, and it has recently been approved for the treatment of soft tissue sarcoma and ovarian cancer. Corey, E. J. J. Am. Chem. Soc. 1996, 118, 9202. (b) Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552. (c) Zhu, J. P. J. Am. Chem. Soc. 2006, 128, 87. (d) Danishefsky, S. J. Angew. Chem., Int. Ed. 2006, 45, 1754. (e) Williams, R. M. J. Org. Chem. 2008, 73, 9594. (f) Fukuyama, T. Synthesis 2012, 44, 2743. (g) Fukuyama, T. J. Am. Chem. Soc. 2013, 135,

3 Corey, E. J. Total Synthesis of Ecteinascidin 743

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10 Zhu, J. P. Total Synthesis of Ecteinascidin 743

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15 Fukuyama, T. Total Synthesis of Ecteinascidin 743

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19 Curtius rearrangement
Strecker reaction

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22 Doyle, M. P. J. Org. Chem. 1979, 44, 1572. Beller, M. Synlett, 1995, 441.

23 Pictet-Spengler reaction


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