Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A.
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Issue Date
2023-03-28Submitted date
2022-02-28
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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 classCitation
Oliver Andler and Uli Kazmaier Organic Letters 2022 24 (13), 2541-2545 DOI: 10.1021/acs.orglett.2c00701Affiliation
Organic Chemistry I, Saarland University, Campus Building C4.2, D-66123 Saarbrücken, GermanyHelmholtz Institute for Pharmaceutical Research Saarland (HIPS), Saarland University, Campus Building C8.1, D-66123 Saarbrücken, GermanyPublisher
ACS/ American Chemical SocietyJournal
Organic lettersPubMed ID
35343704Type
ArticleLetter
Language
enDescription
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 classEISSN
1523-7052Sponsors
Financial support from Saarland University and the DFG (grants: Ka 880/13-1; Bruker Neo 500-447298507) is gratefully acknowledged. We thank Christine Walt from Helmholtz Institute for Pharmaceutical Research Saarland (HIPS) for support with the mass pectrometryae974a485f413a2113503eed53cd6c53
10.1021/acs.orglett.2c00701
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