Asymmetric [4 + 3] cycloadditions between benzofuranyldiazoacetates and dienes: Formal synthesis of (+)-frondosin B
The reaction of benzofuranyldiazoacetates with 1,3-dienes catalyzed by the dirhodium tetracarboxylate Rh2(R-DOSP)4, generates formal [4 + 3] cycloadducts with >94% de and 91-98% ee. The reaction proceeds by a tandem cyclopropanation/
Substituted naphthofurans as hallucinogenic phenethylamine -Ergoline hybrid molecules with unexpected muscarinic antagonist activity
A series of substituted racemic naphthofurans were synthesized as 'hybrid' molecules of the two major prototypical hallucinogenic drug classes, the phenethylamines and the tryptamines/ergolines. Although it was hypothesized that these new agents might pos
Monte, Aaron P.,Marona-Lewicka, Danuta,Lewis, Mechelle M.,Mailman, Richard B.,Wainscott, David B.,Nelson, David L.,Nichols, David E.
Benzofuran Bioisosteres of Hallucinogenic Tryptamines
The benzofuran analogues of the hallucinogens 5-methoxy-N,N-dimethyltryptamine and 5-methoxy-α-methyltryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled
Tomaszewski, Zbigniew,Johnson, Michael P.,Huang, Xuemei,Nichols, David E.
p. 2061 - 2064
(2007/10/02)
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