7770-06-1Relevant academic research and scientific papers
Concise Total Synthesis of Lundurines A-C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
Kirillova, Mariia S.,Muratore, Michael E.,Dorel, Ruth,Echavarren, Antonio M.
, p. 3671 - 3674 (2016)
The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.
Efficient synthesis of optically active α-substituted glutamate analogs possessing α-hydroxymethyl and α-alkoxymethyl groups
Kawasaki, Masanori,Namba, Kosuke,Tsujishima, Hidekazu,Shinada, Tetsuro,Ohfune, Yasufumi
, p. 1235 - 1238 (2007/10/03)
Highly enantioselective synthesis of (2R)-α-(hydroxymethyl)glutamate (1), a selective agonist of mGluR2 and 3, was achieved in short steps using an asymmetric version of the Strecker synthesis. This was converted into its α-methoxymethyl- and α-benzyloxymethyl derivatives 2 and 3, possible ligands as tools to investigate glutamate receptors, via protection of the sterically hindered amino group by means of phase transfer catalyst.
MASS SPECTROMETRIC INVESTIGATION OF CYCLIZATION OF DIAZO COMPOUNDS. XI. CYCLIZATION OF 1-DIAZO-4-METHOXYCARBONYL-2-BUTANONES
Lebedev, A. T.,Kazaryan, A. G.,Sharbatyan, P. A.,Sipyagin, A. M.,Kartsev, V. G.,Petrosyan, V. S.
, p. 1254 - 1259 (2007/10/02)
On the basis of the electron-impact mass spectra of a series of 1-diazo-4-methoxycarbonyl-2-butanones, the data from high-resolution mass spectrometry, and the spectrum of the deuterated analog it was shown that the 2>+. ions formed at the first stage in the fragmentation of the molecular ions of these compounds are partly stabilized with the formation of pseudomolecular ions of oxolanones.The molecular ions of the diazo ketones themselves can dissociate in various directions.The many-path dissociation makes it possible to suppose that the yield of oxolanones formed during cyclization in solution under the influence of acidic agents is small.
