Universität zu Köln

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:	Creators Email ORCID ORCID Put Code Chiha, Slim UNSPECIFIED UNSPECIFIED UNSPECIFIED Spilles, Matthias UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
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:	Keywords Language ACIDS Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/15171