Related Experiment Video
Updated: Feb 11, 2026
![The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F54498.jpg&w=3840&q=50)
The Synthesis of [Sn10SiSiMe334]2- Using a Metastable SnI Halide Solution Synthesized via a Co-condensation Technique
Published on: November 28, 2016
A Novel Aldol Condensation with 2-Methyl-4-pentenal and Its Application to an Improved Total Synthesis of Epothilone
Aaron Balog1, Christina Harris1, Kenneth Savin1
1Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, Box 106, New York, NY 10021 (USA).
Abstract:
The stabilization of the transition state through a favorable interaction between the double bond of 1 and the carbonyl group of 2 appears to be responsible for the high diastereoface selectivity of the aldol reaction. This key step in the highly concise total synthesis of epothilone B is followed by a Suzuki coupling to introduce the thiazole domain, a Noyori reduction to control the stereochemistry at C3, and a final macrolactonization (see reaction scheme). X=protecting group.
More Related Videos
Related Concept Videos
Aldol Condensation vs Claisen Condensation
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation
C–C Bond Formation: Aldol Condensation Overview
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

