Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 10, Pages 1874-1880Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600062
Keywords
Organocatalysis; Enzyme catalysis; Thioureas; Kinetic resolution; Inhibitors
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Funding
- High-Tech Research Center Project for Private Universities from the Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- Japan Society for the Promotion of Science
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A simple and efficient one-pot synthesis of enantiopure hexahydrofuro[2,3-b]furan-3-ol, a crucial component of HIV-1 protease inhibitors, was developed. The one-pot process involves an organocatalytic condensation followed by an enzymatic optical resolution. The condensation of 1,2-dihydrofuran and glycolaldehyde was achieved using Schreiner's thiourea catalyst (1 mol-%). A subsequent lipase-catalyzed kinetic resolution gave the target alcohol with >99 % ee. To demonstrate the practicality of this method, Darunavir, an HIV-1 protease inhibitor used to treat multi-drug-resistant HIV, was synthesized.
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