The Chemistry and Biology of Ratjadone

Abstract

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 (see picture). Supporting information for this article is available on the WWW under http://www.chembiochem.com or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.