SYNTHESIS OF (5R*,6R*)-6-(3-(TERT-BUTYLDIMETHYLSILYLOXY)PROP-1-YNYL)-5-HYDROXYPIPERIDIN-2-ONE.

Dau Xuan Duc, Vo Cong Dung

Abstract


The synthesis of racemic (5R*,6R*)-6-(3-(tert-Butyldimethylsilyloxy)prop-1-ynyl)-5-hydroxypiperidin-2-one was accomplished in 10.3% overall yield over 7 steps. The key steps involved a Sonogashira coupling reaction to make an ene-yne ester and an azidolysis reaction of an epoxide ester to form a γ-lactone.


Keywords


piperidinone, azide, Stemona alkaloids, epoxidation

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Published by Vietnam Academy of Science and Technology