Total Synthesis of Aplyviolene

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Presentation transcript:

Total Synthesis of Aplyviolene M. J. Schnermann and L. E. Overman, J. Am. Chem. Soc. 2011, 133, 16425-16427.

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, 3204-3206.

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, 1846-1848.

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, 4851-4852. M. J. Schnermann, C. M. Beaudry, A. V. Egorova, R. S. Polishchuk, C. Sütterlin and L. E. Overman, PNAS 2010, 107, 6158-6163. 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, 17494-17503.

S. V. Ley, D. J. Dixon, R. T. Guy, F. Rodriguez and T. D. Sheppard, Org. Biomol. Chem. 2005, 3, 4095-4097.