Diastereoselective synthesis of an advanced intermediate of the crocacin family using asymmetric transfer hydrogenation-DKR and Marshall allenylation as key reactions

The natural product of a crocacin-family structural scaffold bearing consecutive anti-anti-syn stereogenic centers was accomplished by means of ATH-DKR and Marshall allenylation reactions with high stereo-control levels. The salient feature of this process is that a single catalytic asymmetric Ru-complex was used for the chirality genesis of pivotal reactions with a high substrate-to-catalyst ratio. (C) 2015 Elsevier Ltd. All rights reserved.