Related Experiment Video
Updated: Sep 27, 2025

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Taming Shapeshifting Anions: Total Synthesis of Ocellatusone C
Andre Sanchez1, Thomas J Maimone1
1Department of Chemistry, University of California─Berkeley, 826 Latimer Hall, Berkeley, California 94720, United States.
Abstract:
Guided by a synthetic design aimed at late-stage diversification, we report the preparation of unusual shapeshifting anions and their subsequent application to the total synthesis of the polyketide natural product ocellatusone C. Site-selective core functionalization of a readily accessible bicyclo[3.3.1]nonane architecture sets the stage for shape-selective side chain installation via a nonfluxional π-allyl Pd-complex derived from a barbaralyl-type anion. Several interesting chemical findings, including substituent-dependent bridged bicycloisomerism and the isolation of a stabilized, 3° carbon-bound Pd-ketone enolate complex, are reported.
Related Concept Videos
Formation of Complex Ions
π Molecular Orbitals of the Allyl Cation and Anion
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Enolate Mechanism Conventions
Ion Exchange
Crown Ethers

