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Total Synthesis of Aplyviolene

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Presentation on theme: "Total Synthesis of Aplyviolene"— Presentation transcript:

1 Total Synthesis of Aplyviolene
M. J. Schnermann and L. E. Overman, J. Am. Chem. Soc. 2011, 133,

2 Total Synthesis of Aplyviolene
Isolated from the marine sponge Dendrilla sp. in the Palau marine lakes Unknown biological activity ] B. Sullivan and D. J. Faulkner, J. Org. Chem. 1984, 49,

3 Total Synthesis of Aplyviolene
J. S. Buckleton, P. R. Bergquist, R. C. Cambie, G. R. Clark, P. Karuso and C. E. F. Rickard, Acta Cryst. 1986, 42,

4 Retrosynthetic Analysis
- Synthesized in 14 steps from A in 5.6% overall yield - A synthesized in 11 steps from 3-methyl-2-cyclohexenone in 19% overall yield A. D. Lebsack, L. E. Overman and R. J. Valentekovich, J. Am. Chem. Soc. 2001, 123, M. J. Schnermann, C. M. Beaudry, A. V. Egorova, R. S. Polishchuk, C. Sütterlin and L. E. Overman, PNAS 2010, 107, M. J. Schnermann, C. M. Beaudry, N. E. Genung, S. M. Canham, N. L. Untiedt, B. D. W. Karanikolas, C. Sütterlin and L. E. Overman, J. Am. Chem. Soc. 2011, 133,

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6 S. V. Ley, D. J. Dixon, R. T. Guy, F. Rodriguez and T. D. Sheppard, Org. Biomol. Chem. 2005, 3,

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