Related Experiment Video
Updated: Nov 1, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Total Synthesis of Nortopsentin D via a Late-Stage Pinacol-like Rearrangement
Katarina L Keel1, Jetze J Tepe1
1Michigan State University, Department of Chemistry, 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
Abstract:
Nortopsentin D is part of a class of bis(indole) alkaloids known for their biological activity, including inhibitory activity in tumoral cells and antifungal activity. Herein we describe the first total synthesis of nortopsentin D, in which amidine and dione undergo a pivotal condensation and subsequent cyclization via a pinacol-like rearrangement. This synthesis represents a unique strategy for the formation of 5,5-disubstituted (4H)-imidazol-4-one containing natural products, many of which have yet to succumb to total synthesis.
More Related Videos
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
10:22Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
Published on: November 30, 2020
Related Concept Videos
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.
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
SN1 Reaction: Stereochemistry
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...