208037-76-7Relevant articles and documents
DIAMINOCYCLOHEXANE COMPOUNDS AND USES THEREOF
-
Paragraph 00362, (2013/03/26)
The present invention provides compounds of Formula (I), or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are agonists, partial agonists and modulators of the NPY Y4 rece
Enantiospecific Synthesis of Natural (-)-Cocaine and Unnatural (+)-Cocaine from D- And L-Glutamic Acid
Lin, Ronghui,Castells, Josep,Rapoport, Henry
, p. 4069 - 4078 (2007/10/03)
Natural (-)-cocaine and unnatural (+)-cocaine have been synthesized enantiospecifically from D-and L-glutamic acid, respectively. The axial-equatorial substitutents were introduced by a stereo-and regiospecific dipolar cycloaddition to the corresponding (1R,5S)- and (1S,5R)-N-BOC-nortropenes with (ethoxycarbonyl)formonitrile N-oxide. A sequence of subsequent stereochemically controlled transformations converted the fused isoxazoline to the requisite β-hydroxy ester. Synthesis of the key intermediate N-BOC-nortropenes involved construction of the 8-azabicyclo[3.2.1]octane framework by Dieckmann condensation of cis-5-substituted D- and L-proline esters. For comparison, (1R,5S)-N-BOC-nortropene also was derived by degradation from natural cocaine. The cis-5-substituted D- and L-proline esters were obtained by sulfide contraction and subsequent catalytic hydrogenation to induce stereospecifically the C-5 stereochemistry from D- and L-thiopyroglutamate, which in turn were prepared from D- and L-glutamic acids, respectively.