Related Experiment Video
Updated: Nov 7, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis of Desacyl Furanmonogones A and B
Dian Li1, Jinfeng Yang1, Bingyan Liu1
1State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
Abstract:
A strategy for the stereoselective synthesis of desacyl furanmonogones A and B has been achieved. The key steps in this synthesis are (1) an Fe(ClO4)3-mediated oxidative radical cyclization for construction of a cis-fused [5-6]-bicyclic core with a bridged lactone substitute, (2) a phosphorane-mediated rearrangement to convert the cis-fused [5-6]-bicyclic core to the corresponding trans-fused [5-6]-bicyclic core, and (3) a Au-catalyzed cascade reaction for formation of the 4,5-seco-3(2H)-furanone motif.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis

