Vicinal ketoesters - key intermediates in the total synthesis of natural products
Marc Paul Beller1, Ulrich Koert1
1Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35032 Marburg, Germany.
Abstract:
This review summarizes examples for the application of vicinal ketoesters such as α-ketoesters, mesoxalic esters, and α,β-diketoesters as key intermediates in the total synthesis of natural products utilizing their electrophilic keto group as reactive site. Suitable key reactions are, e.g., aldol additions, carbonyl ene reactions, Mannich reactions, and additions of organometallic reagents. The vicinal arrangement of carbonyl groups allows the stabilization of reactive conformations by chelation or dipole control.
More Related Videos
Related Concept Videos
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Esters to β-Ketoesters: Claisen Condensation Mechanism
Aldol Condensation with β-Diesters: Knoevenagel Condensation
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Keto–Enol Tautomerism: Mechanism


