Synthesis of biologically active guaianolides with a trans-annulated lactone moiety

Schall, A. and Reiser, O. (2008) Synthesis of biologically active guaianolides with a trans-annulated lactone moiety. European Journal of Organic Chemistry (14), pp. 2353-2364.

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Abstract

The biosynthetic pathways of sesquiterpene lactones are described in conjunction with recent developments in the total syntheses of various biologically active guaianolides. Different strategies towards the 5,7,5-membered ring system are highlighted. Oxidative diol cleavages, aldol reactions, and intramolecular cyclopropanations were used as key reactions to construct the racemic guaianolide core system. Radical cyclizations, as well as ring closing metathesis, were successfully applied in asymmetric approaches. Biomimetic reactions were also applied as versatile tools for the construction of these highly complex natural products.

Item Type:Article
Additional information (public):Schall, Andreas; Reiser, Oliver
Institutions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number:
ValueType
ISI:000256233400001Web of Science ID
10.1002/ejoc.200700880DOI
Subjects:500 Science > 540 Chemistry & allied sciences
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Owner:Oliver Reiser
Deposited On:09 Feb 2009 11:17
Last Modified:16 Nov 2009 15:40
Item ID:5718
Owner Only: item control page