- A ring-closing metathesis-based approach to the synthesis of (+)-tetrabenazine
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A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.
- Johannes, Manuel,Altmann, Karl-Heinz
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supporting information; experimental part
p. 3752 - 3755
(2012/09/07)
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- Palladium-catalyzed carboxamidation reaction and aldol condensation reaction cascade: A facile approach to ring-fused isoquinolinones
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(Chemical Equation Presented) Palladium-catalyzed carboxamidation reaction and aldol condensation reaction cascade are very useful for the synthesis of various ABC ring substituted fused isoquinolinones.
- Chouhan, Gagan,Alper, Howard
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supporting information; experimental part
p. 4987 - 4990
(2009/05/31)
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- An improved stereocontrolled route to cis-erythrinanes by combined intramolecular Strecker and Bruylants reaction
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Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrin
- Reimann, Eberhard,Ettmayr, Christian
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p. 1143 - 1155
(2007/10/03)
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- Carbopalladation of nitriles: Synthesis of 3,4-disubstituted 2-aminonaphthalenes and 1,3-benzoxazine derivatives by the palladium-catalyzed annulation of alkynes by (2-Iodophenyl)acetonitrile
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Intramolecular carbopalladation of the cyano group has been employed for the synthesis of 3,4-disubstituted 2-aminonaphthalenes. (2-Iodophenyl)acetonitrile reacts with a variety of internal alkynes to afford 2-aminonaphthalenes in high yields with good regioselectivity. The scope and limitations of this process, which proceeds by the intramolecular addition of a vinylpalladium species to the triple bond of the cyano group, have been studied. The annulation of certain hindered propargylic alcohols affords 1,3-benzoxazine derivatives, rather than the expected 2-aminonaphthalenes. The involvement of trialkylamine bases in the formation of these heterocyclic compounds has been established. A proposed mechanism for the synthesis of 1,3-benzoxazine derivatives involves the formation of the expected 2-amino-3-(1-hydroxyalkyl)naphthalenes, followed by their condensation with an iminium ion species formed from the trialkylamine base used in the reaction.
- Tian, Qingping,Pletnev, Alexandre A.,Larock, Richard C.
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p. 339 - 347
(2007/10/03)
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