Enantioselective Total Synthesis of (+)-Amphirionin-4.

ABSTRACT: 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.

SUBMITTER: Ghosh AK 

PROVIDER: S-EPMC5328589 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature