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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of "glycospirostanes" via ring-closing metathesis
Dorota Czajkowska1, Jacek W Morzycki, Rosa Santillan
1Institute of Chemistry, University of Białystok, Piłsudskiego 11/4, Białystok, Poland.
Abstract:
Syntheses of "glycospirostanes" from 3beta-hydroxy-23,24-dinor-5alpha-cholano-22,16-lactone and 3alpha-hydroxy-23,24-dinor-5beta-cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation of the C24-C25 double bond. The obtained final products proved to be simultaneously O- and C-l-arabinopyranosides.
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