ol502849y_si_001.pdf (2.05 MB)
Total Synthesis of Muricadienin, the Putative Key Precursor in the Solamin Biosynthesis
journal contribution
posted on 2014-11-21, 00:00 authored by Juliane Adrian, Christian B. W. StarkThe first total synthesis
of muricadienin, the unsaturated putative
precursor in the biosynthesis of trans- and cis-solamin is described. Key steps in the synthesis are
a chemoselective hydroboration, a Z-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.