Dehydroleucodin: a guaiane-type sesquiterpene lactone

Dehydroleucodin [systematic name: (1S,6S,2R)-9,13-dimethyl-5-methylene-3-oxatricyclo[8.3.0.02,6]trideca-9,12-diene-4,11-dione], C15H16O3, is a guanolide isolated from Artemisia douglasiana. The fused-ring system contains a seven-membered ring that adopts a chair conformation, a fused planar cyclopen...

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Bibliographic Details
Main Authors: Horacio A. Priestap, Khalil A. Abboud, Alvaro E. Velandia, Luis A. Lopez, Manuel A. Barbieri
Format: Article
Language:English
Published: International Union of Crystallography 2011-12-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536811048938
Description
Summary:Dehydroleucodin [systematic name: (1S,6S,2R)-9,13-dimethyl-5-methylene-3-oxatricyclo[8.3.0.02,6]trideca-9,12-diene-4,11-dione], C15H16O3, is a guanolide isolated from Artemisia douglasiana. The fused-ring system contains a seven-membered ring that adopts a chair conformation, a fused planar cyclopentenone ring and a five-membered lactone ring fused in envelope conformation. The absolute structure determined by X-ray analysis agrees with that previously assigned to this compound by NMR studies [Bohlmann & Zdero (1972). Tetrahedron Lett. 13, 621–624] and also with that of leucodine, a closely related guaianolide [Martinez et al. (1988). J. Nat. Prod. 51, 221–228].
ISSN:1600-5368