6. The Chemistry and Biology of Ratjadone
M. Kalesse, M. Christmann, U. Bhatt, M. Quitschalle, E. Claus, A. Saeed, A. Burzlaff, C. Kasper, L. O. Haustedt, E. Hofer, T. Scheper, W. Beil
The total synthesis of ratjadone enables a thorough investigation of its mode of action and of structure–activity relationships. In this highly convergent approach, three subunits are joined together by a Wittig olefination and a selective Heck reaction as the pivotal steps. Diastereomeric ratjadones were synthesized by using enantiomeric subunits. They display a range of biological activities that can be correlated to their overall conformational preferences. The overlay of two diastereomers shows that the configuration at C10 induces a helix-like conformation.