Loading...
Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A.
Andler, Oliver Kazmaier, Uli
Andler, Oliver
Kazmaier, Uli
Citations
Altmetric:
Advisors
Editors
Other Contributors
Issue Date
2023-03-28
Submitted date
2022-02-28
Other Titles
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
Publisher
Journal
PubMed ID
PubMed Central ID
Additional Links
Embedded video
Type
Article
Letter
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
Series/Report no.
ISSN
EISSN
1523-7052
ISBN
ISMN
Gov't Doc #
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
License
Attribution-ShareAlike 4.0 International