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http://hdl.handle.net/2445/127597
Title: | Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C |
Author: | Piccichè, Miriam Pinto, Alexandre Griera Farres, Rosa Bosch Cartes, Joan Amat Tusón, Mercedes |
Keywords: | Síntesi asimètrica Lactames Catàlisi asimètrica Asymmetric synthesis Lactams Enantioselective catalysis |
Issue Date: | 15-Dec-2017 |
Publisher: | American Chemical Society |
Abstract: | A synthesis of (+)-gephyrotoxin 287C using, (S)-phenylglycinol-derived tricyclic lactam 7 as the starting enantiomeric scaffold is reported. From the stereochemical standpoint, the key steps are the generation of the DHQ C-5 stereocenter by hydrogenation of the C-C double bond, removal of the chiral inductor to give a cis-DHQ introduction of the DHQ C-2 substituent, completion of the (Z)-enyne moiety, and generation of the C-1 stereocenter during closure of the pyrrolidine ring. |
Note: | Versió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.7b03381 |
It is part of: | Organic Letters, 2017, vol. 19, num. 24, p. 6654-6657 |
URI: | http://hdl.handle.net/2445/127597 |
Related resource: | https://doi.org/10.1021/acs.orglett.7b03381 |
ISSN: | 1523-7060 |
Appears in Collections: | Articles publicats en revistes (Institut de Biomedicina (IBUB)) Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) |
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