Total Synthesis of Muricadienin, the Putative Key Precursor in the Solamin Biosynthesis

2014-11-21T00:00:00Z (GMT) by Juliane Adrian Christian B. W. Stark
The first total synthesis of muricadienin, the unsaturated putative precursor in the biosynthesis of <i>trans</i>- and <i>cis</i>-solamin is described. Key steps in the synthesis are a chemoselective hydroboration, a <i>Z</i>-selective Wittig reaction, and a Fries rearrangement for introducing the terminal α-substituted butenolide. Thus, muricadienin can be synthesized in 11 steps from commercially available starting materials in 42% overall yield.