Related Experiment Video
Updated: Dec 3, 2025

A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Unified Total Synthesis of Five Bufadienolides
Shinsuke Shimizu1, Koichi Hagiwara1, Hiroaki Itoh1
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Abstract:
We report a unified total synthesis of five bufadienolides: bufalin (1), bufogenin B (2), bufotalin (3), vulgarobufotoxin (4), and 3-(N-succinyl argininyl) bufotalin (5). After the steroidal ABCD ring 8 was produced, the D ring was cross-coupled with a 2-pyrone moiety and stereoselectively epoxidized to generate 6. TMSOTf promoted a stereospecific 1,2-hydride shift from 6 to establish the β-oriented 2-pyrone of 19. Functional group manipulations from 19 furnished 1-5, which potently inhibited cancer cell growth.
More Related Videos
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Five-Membered Heterocyclic Aromatic Compounds: Overview
Biosynthesis of Lipids
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Biosynthesis of Polysaccharides

