Related Experiment Video
Updated: Aug 6, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Construction of a Chasmanine Skeleton Enabled by Hg(OAc)2-Promoted Vinylogous Mannich Reaction
Hibiki Asai1, Shu Nakamura1, Koichi Hagiwara1
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo113-0033, Japan.
None:
Chasmanine and puberuline C share a hexacyclic ABCDEF-ring but differ in the fusion pattern of their 5- and 6-membered F-rings. Here, we present a novel strategy for constructing the chasmanine skeleton, starting from a key intermediate employed in our total synthesis of puberuline C. Following optimization of a radical cyclization to build the ABCE-ring system, Hg(OAc)2-promoted vinylogous Mannich and Mukaiyama aldol reactions formed the F- and D-rings, respectively, thereby completing the assembly of the hexacycle.
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
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Related Concept Videos
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction