82273-33-4Relevant academic research and scientific papers
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.
Application of the Nickel-Mediated Neopentyl Coupling in the Total Synthesis of the Marine Natural Product Arenarol
Watson, Anthony T.,Park, Kwangyong,Wiemer, David F.,Scott, William J.
, p. 5102 - 5106 (2007/10/02)
Racemic arenarol (1) has been synthesized from the known decalin 5β-carbethoxy-1,1-(1,2-ethylenedioxy)-5α,8aβ-dimethyl-1,2,3,5,6,7,8,8a-octahydro-6-oxonaphthalene (9) via a short, efficient, and highly stereocontrolled sequence.Key steps in this synthesis are the directed hydrogenation of an unsaturated neopentyl alcohol to provide stereocontrolled formation of the two adjacent tetriary centers and subsequent elaboration of the arenarol skeleton via a nickel-mediated coupling of the corresponding neopentyl iodide.This sequence demonstrates the value of nickel-mediated crosscoupling reactions for carbon-carbon bond formation at neopentyl centers.
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.
