Enantioselective Approach to the Right-Hand Substructure of Solanoeclepin A
SourceEuropean Journal of Organic Chemistry, 35, (2016), pp. 5845-5854
Article / Letter to editor
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Solid State Chemistry
European Journal of Organic Chemistry
SubjectSolid State Chemistry
An enantioselective synthesis of the right-hand substructure of solanoeclepin A has been developed. The key step was an intramolecular [2+2] photocycloaddition between an allene and a butenolide providing a methylenecyclobutane with three quaternary carbon atoms in a complex tetracyclic framework. Other crucial steps included an enantioselective Noyori transfer hydrogenation of a ketone, a diastereoselective silver-mediated silyl dienolate allylation, and a diastereoselective cyclopropanation of an allylic alcohol. The installation of the bridgehead methyl group by reduction of the lactone moiety proved to be troublesome.
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