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Research Article Open access CC BY 4.0

Mechanisms of the Aqueous Solvolysis of the Ring-opening of the Lactone Ring of Goniodomin A

B. Andes Hess Jr., Lidia Smentek

International Research Journal of Pure and Applied Chemistry · pp. 9–16 · Published 28 Nov 2022

10.9734/irjpac/2022/v23i6792

Abstract

The phycotoxin Goniodomin A is a Dinoflagellate of the Alexandrium genus and is a macrocyclic lactone. It is found widely in sea water and is known to open slowly the lactone in water. The cleavage of the lactone is sensitive to the pH of the water. As one changes the pH from ~6 to 8 its solvolytic rate dramatically increases. Treatment of kinetic data previously published indicates that there are two competing first-order reactions, an SN­1 and an intramolecular SN2, which is a pseudo first-order reaction.

Marine phytotoxin mechanism of lactone hydrolysis lactone epoxide carbocation nucleophilic reactions

Cited by 1

Goniodomic Acid, a Transient Oxirane Intermediate in the Conversion of the Macrolide Algal Toxin Goniodomin A to Seco Acids

Constance M. Harris, Bernd Krock, Thomas M. Harris · Chemical Research in Toxicology · 2024

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