Related Experiment Video
Updated: Mar 29, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Bioinspired Synthesis of a Sedaxane Metabolite Using Catalytic Vanadyl Acetylacetonate and Molecular Oxygen
Sameer Tyagi1, Christopher D Cook1, Dana A DiDonato1
1Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
Abstract:
A bioinspired synthesis of the sedaxane metabolite 2 from intermediate 3 using catalytic VO(acac)2 and O2 is described. Intermediate 3 was synthesized starting from 2-bromostyrene in four steps. The inner cyclopropyl ring of 3 was assembled with trans geometry using a highly diastereoselective Nishiyama cyclopropanation, and the outer hydroxycyclopropyl ring was installed using the Kulinkovich cyclopropanation. Additionally, conversion of 3 into 2 was demonstrated in in vitro microbial culture experiments consisting of bacteria and fungi.
Related Concept Videos
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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

