TY - DATA T1 - Enantioselective Total Synthesis of (+)-Amphirionin‑4 PY - 2016/04/26 AU - Arun K. Ghosh AU - Prasanth R. Nyalapatla UR - https://acs.figshare.com/articles/journal_contribution/Enantioselective_Total_Synthesis_of_Amphirionin_4/3201772 DO - 10.1021/acs.orglett.6b00942.s001 L4 - https://ndownloader.figshare.com/files/5025928 KW - functionalized tetrahydrofuran KW - amphirionin KW - diastereoselective syn KW - convergent manner KW - synthesis features KW - allylation reaction KW - tetrahydrofuranol core KW - lipase resolution KW - polyene side chain N2 - 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 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. ER -