Enantioselective Total Synthesis of (+)-Amphirionin‑4

2016-04-26T00:00:00Z (GMT) by Arun K. Ghosh Prasanth R. Nyalapatla
An enantioselective total synthesis of (+)-amphirionin-4 has been accomplished in a convergent manner. The synthesis features an efficient enzymatic lipase resolution to access the tetrahydrofuranol core in optically active form. The functionalized tetrahydrofuran derivative was synthesized via an oxocarbenium ion-mediated highly diastereoselective <i>syn</i>-allylation reaction. The polyene side chain was synthesized using Stille coupling reactions. Nozaki–Hiyama–Kishi coupling was utilized to construct the C-8 stereocenter and complete the synthesis of (+)-amphirionin-4.