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Updated: May 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Formal synthesis of merrilactone A using a domino cyanide 1,4-addition-aldol cyclization
Naim Nazef1, Robert D M Davies, Michael F Greaney
1School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K., School of Chemistry, University of Edinburgh , Joseph Black Building, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, U.K., and AstraZeneca , Mereside, Alderley Park, Macclesfield, Cheshire SK10 4TG, U.K.
Abstract:
A formal synthesis of merrilactone A has been completed using a domino 1,4-addition-aldol process as the key step. Both iodo- and cyano-1,4-addition-aldol cyclizations were productive in forming the highly hindered C1-C9 bond linking vic-quaternary and tertiary stereocenters. The latter method was used to complete a formal total synthesis of the natural product.
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