Related Experiment Video
Updated: Sep 21, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Preparation of a ε-caprolactonic diterpenoid derivate by unexpected oxidative cleavage/lactonization of
Pablo A Chacón-Morales1, Juan M Amaro-Luis2, Luis Beltrán Rojas Fermín3
1Natural Products Laboratory, Department of Chemistry, Faculty of Science, University of Los Andes, Mérida, 5101, Venezuela. pablochacon1@gmail.com.
Abstract:
From aerial parts of Austroeupatorium inulifolium was isolated the ent-nor-furano triol labdane austroeupatol 1. The compound 1 was treated with IBX showing an unexpected selectivity at the potentially oxidizable sites of the substrate yielding the 2-oxoaustroeupatol (2) and 2,19-dioxoaustroeupatol (3). The treatment of 2 with sodium periodate yields a heterocyclic derivative (ε-caprolactone derivate 4) formed by oxidative cleavage and unexpected intramolecular attack of the hydroxymethylene (C-19) oxygen to the ketonic carbon (C-2). A plausible mechanistic pathway for the obtention of compound 4 is proposed.
More Related Videos
Related Concept Videos
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
Preparation of Carboxylic Acids: Overview
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Alkynes to Carboxylic Acids: Oxidative Cleavage

