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Enantioselective Total Synthesis of (+)-Amphirionin‑4

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journal contribution
posted on 2016-04-26, 00:00 authored 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 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.

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