Vinylogous Mukaiyama Aldol Reactions in the Total Syntheses of Natural Products


Natural products are a rich source of bioactive compounds, which are used for medical applications. In most cases, the biological activity is controlled by the overall conformation of natural products which in turn is a result of their chiral centers. We will describe our contributions towards controlling the configuration of chiral centers and the rapid assembly of polyketides using the vinylogous Mukaiyama aldol reaction. Natural products that are covered are ratjadone,1 tedanolide,2 angiolam,3 kulkenon,4 lipomycin5 and aetheramide.6

[1] Total Synthesis of (+)-Ratjadone, M. Christmann, U. Bhatt, M. Quitschalle, E. Claus, M. Kalesse, Angew. Chem. 2000, 112, 4535-4538; Angew. Chem. Int. Ed. 2000, 39, 4364-4366.
[2] The Total Synthesis of (+)-Tedanolide, G. Ehrlich, J. Hassfeld, U. Eggert, M. Kalesse, J. Am. Chem. Soc. 2006, 128, 14038-14039.
[3] Synthesis of Angiolam A, M. T. Gieseler, M. Kalesse, Org. Lett. 2014, 16, 548-551.
[4] Structure Elucidation and Total Synthesis of Kulkenon, G. Symkenberg, M. Kalesse, Angew. Chem. Int. Ed., 2014, 53, 1795-1798.
[5] Structure Elucidation and Total Synthesis of β-Lipomycin, O. Hartmann, M. Kalesse, Angew. Chem. 2014, 126, 7463–7466; Angew. Chem. Int. Ed. 2014, 53, 7335-7338.
[6] Total Synthesis of Aetheramide A, L. Gerstmann, M. Kalesse Chem. Eur. J. 2016, 32, 11210-11212.

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