Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A

Andler, Oliver; Kazmaier, Uli

Please use this identifier to cite or link to this item: doi:10.22028/D291-43394

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Title:	Stereoselective Synthesis of a Protected Side Chain of Meliponamycin A
Author(s):	Andler, Oliver Kazmaier, Uli
Language:	English
Title:	Organic Letters
Volume:	24
Issue:	13
Pages:	2541-2545
Publisher/Platform:	ACS
Year of Publication:	2022
Free key words:	Metabolism Organic Compounds Pharmaceuticals Redox Reactions Substituents
DDC notations:	500 Science
Publikation type:	Journal Article
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.
DOI of the first publication:	10.1021/acs.orglett.2c00701
URL of the first publication:	https://pubs.acs.org/doi/10.1021/acs.orglett.2c00701
Link to this record:	urn:nbn:de:bsz:291--ds-433940 hdl:20.500.11880/38910 http://dx.doi.org/10.22028/D291-43394
ISSN:	1523-7052 1523-7060
Date of registration:	7-Nov-2024
Description of the related object:	Supporting Information
Related object:	https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.2c00701/suppl_file/ol2c00701_si_001.pdf
Faculty:	NT - Naturwissenschaftlich- Technische Fakultät
Department:	NT - Chemie
Professorship:	NT - Prof. Dr. Uli Kazmaier
Collections:	SciDok - Der Wissenschaftsserver der Universität des Saarlandes

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