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
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: |
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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: | Faculty of Mathematics and Natural Sciences | ||||||||||||||||||||
Divisions: | Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry | ||||||||||||||||||||
Subjects: | no entry | ||||||||||||||||||||
Uncontrolled Keywords: |
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Refereed: | Yes | ||||||||||||||||||||
URI: | http://kups.ub.uni-koeln.de/id/eprint/15171 |
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