Related Experiment Video
Updated: Sep 30, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Biomimetic synthesis of petuniasterone D via the epoxy ester[bond]ortho ester rearrangement
Juan A Faraldos1, José-Luis Giner
1Department of Chemistry, SUNY-ESF, Syracuse, New York 13210, USA.
Abstract:
The side chain of the insecticidal steroid petuniasterone D was synthesized by the biomimetic acid-catalyzed epoxy ester[bond]ortho ester rearrangement. In addition to the natural (22R,24R)-configuration of the side chain ortho ester, compounds bearing the epimeric (22R,24S)-, (22S,24R)-, and (22S,24S)- [3.2.1]-bicyclic ortho esters were also produced by stereospecific rearrangement of the corresponding isomeric epoxy esters. Functionalization of the steroid nucleus of the (22R,24R)-ortho ester completed the synthesis of the natural product.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry