Related Experiment Video
Updated: Feb 28, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Bioinspired Synthesis of Curtachalasin A and Δ6,12-Curtachalasin N Enabled by Tandem Transannular Epoxyalkene
Hanwei Li1, Jiao Yao2, Ya Liu1
1Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming 650500, China.
Abstract:
Biomimetic syntheses of curtachalasin A (1) and Δ6,12-curtachalasin N (12), a highly oxidized rearranged cytochalasin-type featuring a novel 5/6/6/6 tetracyclic scaffold converted from naturally abundant cytochalasin D containing a 5/6/11 tricyclic skeleton, were first achieved efficiently in three and four steps, respectively. The conversion route features three pivotal transformations involving selective Prilezhaev epoxidation, acid-mediated tandem transannular epoxyalkene cyclization, and a subsequent spontaneous α-ketol rearrangement. This work provides an efficient approach to access the naturally occurring scarce curtachalasin A, paving the way for the syntheses of other members of the curtachalasins family and revealing the potential biosynthetic relationship between cytochalasins and curtachalasins in a chemical perspective.
More Related Videos
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Cycloaddition Reactions: Overview
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Thermal and Photochemical Electrocyclic Reactions: Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation