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Enantioselective Synthesis of the Antiinflammatory Agent (−)-Acanthoic Acid
Ist Teil von
Journal of organic chemistry, 2001-12, Vol.66 (26), p.8843-8853
Ort / Verlag
United States: American Chemical Society
Erscheinungsjahr
2001
Link zum Volltext
Quelle
MEDLINE
Beschreibungen/Notizen
An enantioselective synthesis of the potent antiinflammatory agent (−)-acanthoic acid (1) is described. The successful strategy departs from (−)-Wieland−Miescher ketone (10), which is readily available in both enantiomeric forms and constitutes the starting point toward a fully functionalized AB ring system of 1. Conditions were developed for a regioselective double alkylation at the C4 center of the A ring, which produced compound 32 as a single stereoisomer. Construction of the C ring of 1 was accomplished via a Diels−Alder reaction between sulfur-containing diene 43 and methacrolein (36), which after desulfurization and further functionalization yielded synthetic acanthoic acid. The described synthesis confirms the proposed stereochemistry of the natural product and represents a fully stereocontrolled entry into an underexplored class of biologically active diterpenes.