Related Experiment Video
Updated: Jun 25, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Toward the Briarane Core via 1,3-Dipolar Cycloaddition
Yichen Liu1,2, Jiangang Zhao1,2, Ran Hong1,2
1State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P.R. China.
Abstract:
The complete C20 framework of brianthein W was established, featuring hydroboration/allylation, to provide the C1-C2 quaternary/tertiary stereoarray with excellent stereocontrol. Intramolecular nitrile oxide cycloaddition (INOC) was adopted as the key transformation to establish the trans-fused 6/10-bicyclic ring system. Evolution of the second INOC event revealed the intricacies governing regioselectivity, which ultimately led to construction of the highly strained 10-membered carbocycle.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: Overview
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
β-Dicarbonyl Compounds via Crossed Claisen Condensations

