Journal
ORGANIC LETTERS
Volume 18, Issue 9, Pages 2296-2299Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00942
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Funding
- National Institutes of Health
- Purdue University
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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 Stile 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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