The enantioselective synthesis of spiro architecture often associated with significant biological activity, render the spiro [pyrrolidine-3, 3-oxindole] alkaloids as an appealing synthetic target. We envisioned a novel approach of preparing 3,3-disubstituted oxindole from an acyclic stereogenic center. Consequently, we have screened three-way approaches of Pd AAA, (i) addition of Pd-L*-allyl electrophile to acrylate, (ii) using O-allyl ether acrylate as a nucleophile, and (iii) in situ generation of enolate nucleophile by decarboxylation of carboxyallyl acrylate. Based on that thorough optimization on O-NO<sub>2</sub> substituted 3-hydroxy aryl acrylate, we obtained enantioselectivity up to 85%. Using the best method, we then prepared the tetra substituted oxindole and developed a 6 step shortest synthetic protocol for the asymmetric synthesis of (-)-Coerulescine (isolated from the blue canary grass <i>Phlaris coerulescens"</i>) with 40% overall yield. This approach can offer us an innovative tool and solution for the systematic and large-scale synthesis of target drug molecule.

Palladium-catalyzed asymmetric allylic alkylation of ortho nitro hydroxy acrylate: total synthesis of (-)-coerulescine

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.