Chiha, Slim, Spilles, Matthias, Neudoerfl, Joerg-Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2019). A Stereoselective Synthesis of the ACE Inhibitor Trandolapril. Synlett, 30 (7). S. 813 - 817. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the -allylation of a protected l -pyroglutamic acid derivative, a highly diastereoselective Hosomi-Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Chiha, SlimUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Spilles, MatthiasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-151715
DOI: 10.1055/s-0037-1612306
Journal or Publication Title: Synlett
Volume: 30
Number: 7
Page Range: S. 813 - 817
Date: 2019
Publisher: GEORG THIEME VERLAG KG
Place of Publication: STUTTGART
ISSN: 1437-2096
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
ACIDSMultiple languages
Chemistry, OrganicMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/15171

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