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https://hdl.handle.net/2445/127382| Title: | Biomimetic Construction of the Hydroquinoline Ring System. Diastereodivergent Enantioselective Synthesis of 2,5-Disubstituted cis-Decahydroquinolines |
| Author: | Amat Tusón, Mercedes Fabregat, Robert Griera Farres, Rosa Florindo, Pedro Molins i Grau, Elies Bosch Cartes, Joan |
| Keywords: | Biosíntesi Biomimètica Síntesi asimètrica Síntesi orgànica Biosynthesis Biomimetics Asymmetric synthesis Organic synthesis |
| Issue Date: | 31-Mar-2010 |
| Publisher: | American Chemical Society |
| 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. |
| Note: | Versió postprint del document publicat a: https://doi.org/10.1021/jo1005894 |
| It is part of: | Journal of Organic Chemistry, 2010, vol. 75, num. 11, p. 3797-3805 |
| URI: | https://hdl.handle.net/2445/127382 |
| Related resource: | https://doi.org/10.1021/jo1005894 |
| ISSN: | 0022-3263 |
| Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) Articles publicats en revistes (Institut de Biomedicina (IBUB)) |
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|---|---|---|---|---|
| 579354.pdf | 308.9 kB | Adobe PDF | View/Open |
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