Title:
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Biomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines
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Author:
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Amat Tusón, Mercedes; Fabregat, Robert; Griera Farres, Rosa; Florindo, Pedro; Molins i Grau, Elies; Bosch Cartes, Joan
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Other authors:
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Universitat de Barcelona |
Abstract:
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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 occur in nature in the biosynthesis of amphibian decahydroquinoline alkaloids. Diastereodivergent routes to enantiopure cis-2,5-disubstituted decahydroquinolines, including the alkaloid pumiliotoxin C (cis-195A), are developed. |
Subject(s):
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-Biosíntesi -Biomimètica -Síntesi asimètrica -Síntesi orgànica -Biosynthesis -Biomimetics -Asymmetric synthesis -Organic synthesis |
Rights:
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(c) American Chemical Society , 2010
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Document type:
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Article Article - Accepted version |
Published by:
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American Chemical Society
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