ol6b00942_si_001.pdf (2.35 MB)
Enantioselective Total Synthesis of (+)-Amphirionin‑4
journal contribution
posted on 2016-04-26, 00:00 authored by Arun K. Ghosh, Prasanth R. NyalapatlaAn
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 syn-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.