Add time:07/12/2019 Source:sciencedirect.com
A concise synthesis of the β-amyloid1–42 aggregation inhibitor (−)-5,8-dihydroxy-3R-methyl-2R-(dipropylamino)-1,2,3,4-tetrahydronaphthalene [(−)-2] has been developed. The key step is a regio- and diastereoselective hydroboration-amination sequence to convert alkene 6 into amine 9. Enantiomeric resolution was achieved by recrystallization of amine 9 as the dibenzoyl-d-tartaric acid salt. Hydroquinone 2 is a potent inhibitor of the fibrillar aggregation of β-amyloid as determined in two different assay systems.
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