Related Experiment Video
Updated: Aug 6, 2026

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Total Synthesis of Benthol A: The Nominal and the Actual Natural Product
Guanghao Huang1, Andrea Tomio1, Thomas Varlet1
1Max-Planck-Institut für Kohlenforschung, 45470Mülheim/Ruhr, Germany.
Abstract:
The total synthesis of the dinoflagellate-derived "super-carbon-chain compound" benthol A rigorously confirmed what the analysis of one of the required building blocks had forecasted, namely that the configuration of the secondary -OH group at C40 had been misassigned by the isolation team as the only one of a total of 35 stereogenic centers decorating the backbone of this polyol/polyether derivative. This conclusion bears implications because the original assignment had been solely based on computational data, which had resulted in a remarkably high score of 99.93% that was ultimately misleading. The multiconvergent blueprint underlying the successful approach accounts for the fact that alongest linear sequence of 32 steps sufficed to reach this intricate marine natural product. The inherent flexibility should also empower future studies aiming at a detailed mapping of the pharmacophore of this compound endowed with significant antiplasmodial activity.
Related Concept Videos
¹H NMR: Complex Splitting
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied first.
¹H NMR Signal Integration: Overview
Directing and Steric Effects in Disubstituted Benzene Derivatives
NMR Spectroscopy of Benzene Derivatives
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
β-Dicarbonyl Compounds via Crossed Claisen Condensations

