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A Highly Stereoselective Divergent Synthesis of Bicyclic Models of Photoreactive Sesquiterpene Lactones
Author(s) -
Fuchs Sébastien,
Berl Valérie,
Lepoittevin JeanPierre
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600611
Subject(s) - chemistry , sesquiterpene , moiety , stereoselectivity , allylic rearrangement , bicyclic molecule , methylene , enantiomer , stereochemistry , reactivity (psychology) , enantioselective synthesis , organic chemistry , catalysis , medicine , alternative medicine , pathology
Sesquiterpene lactones are natural stereochemically pure compounds, which show a number of biological activities. In order to study the reactivity of sesquiterpene lactones in biological systems, we describe herein the asymmetric synthesis of a simple model, the α‐methylene‐hexahydrobenzofuranone 1 , which includes the α‐methylene‐γ‐butyrolactone moiety and presents all the different possible ring junctions. Enantioselectivity was obtained by asymmetric palladium‐catalyzed allylic substitution, and diastereoselectivity was achieved by iodolactonization. This strategy afforded the different lactones with an enantiomeric excess of >98 %. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)