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Updated: Sep 28, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A
Oliver Andler1, Uli Kazmaier1,2
1Organic Chemistry I, Saarland University, Campus Building C4.2, D-66123 Saarbrücken, Germany.
Abstract:
The Matteson homologation was found to be a versatile tool for the construction of the linear polyketide side chain of meliponamycin and related compounds in only four steps. The ester dienolate version of this reaction allowed the introduction of the unsaturated ester moiety in a highly stereoselective fashion. Boronate oxidation/deoxygenation and Sharpless dihydroxylation are additional key steps in the stereoselective construction of this highly functionalized tetrahydropyran ring system, which is characteristic of this substance class.
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