53723-52-7Relevant articles and documents
The total syntheses of basiliolide C, epi-basiliolide C, and protecting-group-free total syntheses of transtaganolides C and D
Gordon, Jonny R.,Nelson, Hosea M.,Virgil, Scott C.,Stoltz, Brian M.
, p. 9740 - 9747 (2014)
The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland-Claisen/Diels-Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three rings, two all-carbon quaternary centers, and four tertiary stereocenters from a monocyclic, achiral precursor. (Chemical Equation Presented).
Rhodium-catalyzed oxygenative addition to terminal alkynes for the synthesis of esters, amides, and carboxylic acids
Kim, Insu,Lee, Chulbom
supporting information, p. 10023 - 10026 (2013/10/01)
A gem of a couple: The title reaction of terminal alkynes with O and Nnucleophiles proceeds in the presence of [Rh(cod)Cl}2], P(4-FC 6H4)3, and 4-picoline N-oxide. Alcohols, amines, and water add to the terminal alkynes to give esters, amides, and carboxylic acids, respectively. The reaction involves formation of a rhodium vinylidene, oxidation to a ketene by oxygen transfer, and nucleophilic addition.
Asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters with trisubstituted C=C bonds - Enantioselective syntheses of trisubstituted γ-butyrolactones
Kapferer, Tobias,Brueckner, Reinhard
, p. 2119 - 2133 (2007/10/03)
β,γ-Unsaturated esters with stereodefined trisubstitued C=C double bonds were prepared by the Arndt-Eistert homologation of α,β-unsaturated carboxyl halides, by two-step methoxycarbonylation of allylbarium reagents, by deconjugation of α,β-unsaturated esters, and by Horner-Wadsworth-Emmons variants of the Stobbe condensation. Sharpless asymmetric dihydroxylation of the β,γ-unsaturated esters, followed by spontaneous cyclization, afforded β-hydroxy-γ-lactones in moderate to good yields and with enantiomeric excesses of up to 97 %. Similarly, tetrahydroxy-γ-lactones were obtained from diunsaturated esters; these lactones were converted into a bislactone and an unsaturated β-hydroxy γ-lactone. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.