Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A.

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Authors
Andler, Oliver
Kazmaier, Uli
Issue Date
2023-03-28
Submitted date
2022-02-28

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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
Citation
Oliver Andler and Uli Kazmaier Organic Letters 2022 24 (13), 2541-2545 DOI: 10.1021/acs.orglett.2c00701
Affiliation
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, Germany
Publisher
ACS/ American Chemical Society
Journal
Organic letters
URI
http://hdl.handle.net/10033/623174
DOI
10.1021/acs.orglett.2c00701
PubMed ID
35343704
Type
Article
Letter
Language
en
Description
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
EISSN
1523-7052
Sponsors
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 pectrometry
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Except where otherwise noted, this item's license is described as Attribution-ShareAlike 4.0 International