Related Experiment Video
Updated: Aug 18, 2026

Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
Published on: June 28, 2019
Total synthesis of 12,13-desoxyepothilone B (Epothilone D)
Robert L Broadrup1, Hema M Sundar, Charles S Swindell
1Protarga, Inc., King of Prussia, PA 19406, USA. organicrob@comcast.net
Abstract:
A highly convergent total synthesis of 12,13-desoxyepothilone B (4, Epothilone D) is described involving the coupling of vinyl iodide (5) and olefin (6). Key steps in the synthesis are the introduction of chirality at C15 via highly enantioselective lipase-mediated enzymatic resolution, diastereoselective alkylation at C8, highly diastereoselective Evans aldol reaction to establish C6-C7, and Mukaiyama aldol reaction to introduce chiral center C3. Palladium catalyzed Suzuki coupling of (5) and (6) provided the methyl ester (27), which was converted to 12,13-desoxyepothilone B (4).
More Related Videos
Related Concept Videos
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Sharpless Epoxidation
Structure and Nomenclature of Epoxides
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Base-Catalyzed Ring-Opening of Epoxides
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

