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Updated: Jul 7, 2026

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Total synthesis of (+)-pinnatoxin A
Craig E Stivala1, Armen Zakarian
1Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
Abstract:
A convergent enantioselective total synthesis of (+)-pinnatoxin A is described. The synthesis capitalizes on the highly diastereoselective Ireland-Claisen rearrangement of an acyclic alpha-branched allylic ester to set the quaternary stereogenic center at the core of the spiroimine ring system along with the adjacent tertiary stereocenter. The all-carbon macrocyclic ring system was formed by ring-closing metathesis.
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