Related Experiment Video
Updated: Sep 13, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthetic Study of Caulerpin: Construction of the Core Structure through Gold-Catalyzed Cascade Cyclization of
Hiroaki Ohno1, Atsuhito Tsuji1, Daiki Hasegawa1
1Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Abstract:
In this synthetic study, a gold-catalyzed cascade cyclization reaction for the construction of the caulerpin scaffold, suitable for the preparation of unsymmetrical caulerpin derivatives, was developed. The reaction proceeds through the formation of an α-imino gold(I) carbene from an azido-alkyne, followed by nucleophilic attack of an alkenylindole moiety on the gold carbene, leading to the formation of the bis-indole-fused 8-membered ring, the caulerpin core structure. The use of ethyl enol ether and a bulky phosphine ligand is suitable for successful ring closure at the desired position.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)