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2010-03-31

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/127382

Biomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines

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Abstract

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.

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https://doi.org/10.1021/jo1005894

Subject

Biosíntesi, Biomimètica, Síntesi asimètrica, Síntesi orgànica

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Biosynthesis, Biomimetics, Asymmetric synthesis, Organic synthesis

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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AMAT TUSÓN, Mercedes, et al. Biomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines. Journal of Organic Chemistry. 2010. Vol. 75, num. 11, pags. 3797-3805. ISSN 0022-3263. [consulted: 13 of October of 2026]. Available at: https://hdl.handle.net/2445/127382

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