Related Experiment Video
Updated: Jan 15, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Enantioselective Synthesis of the Proposed Structure of (-)-Taiwaniadduct F
Debgopal Jana1, Suman Noskar1, Monosij Nandy1
1Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur Campus, Kalyani, Nadia 741 246, West Bengal, India.
Abstract:
The first enantioselective synthesis of the reported structure of taiwaniadduct F (2) has been accomplished in a highly regioselective manner through a biomimetic intermolecular [5+2] cycloaddition under extremely mild conditions where trans-ozic acid methyl ester (4a) serves as the dipolarophile and a p-benzoquinone of abeo-abietane (20) acts as the 1,5-dipole. In the process, herein, we document the first instance of an oxy-acyloin rearrangement that results in skeleton reassembly of a [6-5-6-5] scaffold into a [6-6-5-6] framework. The absolute configuration was confirmed using X-ray crystallography of advanced intermediates along with detailed 2D NMR analysis.
More Related Videos
12:31Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
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...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Cycloaddition Reactions: Overview
Sharpless Epoxidation