Biomimetic construction of the hydroquinoline ring system. Diastereodivergent enantioselective synthesis of 2,5-disubstituted cis -decahydroquinolines
Figure presented The straightforward enantioselective construction of the hydroquinoline ring system from 1,5-polycarbonyl derivatives, using (R)-phenyglycinol as a chiral latent form of ammonia, is reported. The process mimics the key steps believed to o
Amat, Mercedes,Fabregat, Robert,Griera, Rosa,Florindo, Pedro,Molins, Elies,Bosch, Joan
scheme or table
p. 3797 - 3805
(2010/08/20)
A biomimetic enantioselective approach to the decahydroquinoline class of dendrobatid alkaloids
(Chemical Equation Presented) A princely synthesis: The hypothetical key step in the biosynthesis of the decahydroquinoline dendrobatid alkaloids, such as cis-195 A found in frogs, from 1,5-polycarbonyl derivatives is mimicked by using (R)-phenylglycinol as a chiral latent form of ammonia in a double cyclocondensation reaction.
Amat, Mercedes,Griera, Rosa,Fabregat, Robert,Molins, Elies,Bosch, Joan
p. 3348 - 3351
(2008/12/23)
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