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ABSTRACT:
SUBMITTER: Moore GL
PROVIDER: S-EPMC5437813 | biostudies-literature | 2017 Jan
REPOSITORIES: biostudies-literature
Organic process research & development 20161214 1
A practical synthesis of (3<i>R</i>,3a<i>S</i>,6a<i>R</i>)-hexahydrofuro[2,3-<i>b</i>]furan-3-ol-a key intermediate in the synthesis of darunavir-from monopotassium isocitrate is described. The isocitric acid salt, obtained from a high-yielding fermentation fed by sunflower oil, was converted in several steps to a tertiary amide. This amide, along with the compound's ester functionalities, was reduced with lithium aluminum hydride to give, on acidic workup, a transient aminal-triol. This was con ...[more]