Related Experiment Video
Updated: Jul 17, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
General strategy for the synthesis of B1 phytoprostanes, dinor isoprostanes, and analogs
Annika Schmidt1, Wilhelm Boland
1Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll-Strasse 8, D-07745 Jena, Germany.
Abstract:
The synthesis of the phytoprostane B1 types I and II is achieved in high overall yield (35-53%) by only two principal transformations starting from 1,3-cyclopentanedione. The first side chain is attached via O-acylation of the 1,3-dione followed by rearrangement and reduction to give the 2-alkyl-1,3-diones 4a-c. After conversion into the corresponding vinylic iodides 5a-c, the second side chain is introduced by transition metal catalysis following Heck- or Sonogashira-type protocols. The whole spectrum of the phytoprostane B1 types I, II, and the dinor isoprostane B1 type III and some structural analogs are rapidly accessible along the same general protocol.
More Related Videos
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Stability of Conjugated Dienes
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

