1173666-35-7Relevant articles and documents
Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid
Ling,Chowdhury,Kramer,Vong,Palladino,Theodorakis
, p. 8843 - 8853 (2007/10/03)
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.
Effects of γ-hydroxyl groups in lithium-ammonia reductions of α,β-unsaturated carbonyl compounds via an inverse-addition, low-temperature method
Groot, Ae. de,Jansen, B. J. M.,Peterse, A. G. J. M.,Wijnberg, J. B. P. A.
, p. 177 - 180 (2007/10/02)
A new inverse-addition, low-temperature procedure for lithium-ammonia reductions has been developed.Using this method it has been demonstrated that the reduction of ethyl 5,5-(ethylenedioxy)-8β-hydroxy-4aβ-methyl-2-oxo-2,3,4,4a,5,6,7,8-octahydro-1-naphthalenecarboxylate (3) results in an unusual cis-reduction product.The 8β-hydroxyl group, low reaction temperature (-80 deg C) and addition of lithium-ammonia to the substrate all proved to be necessary in order to achieve this cis reduction.
