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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

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

Ghosh Arun K AK Nyalapatla Prasanth R PR

Organic letters 20160426 9

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 constru ...[more]

PMID: 27116318

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