Biomimetic Total Synthesis of Dysoxylum Alkaloids.
| Autor: | Puerto Galvis CE; Laboratorio de Química Orgánica y Biomolecular, CMN , Universidad Industrial de Santander , Parque Tecnológico Guatiguará, Km 2 Vía Refugio , Piedecuesta 681011 , Colombia., Kouznetsov VV; Laboratorio de Química Orgánica y Biomolecular, CMN , Universidad Industrial de Santander , Parque Tecnológico Guatiguará, Km 2 Vía Refugio , Piedecuesta 681011 , Colombia. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2019 Dec 06; Vol. 84 (23), pp. 15294-15308. Date of Electronic Publication: 2019 Nov 15. |
| DOI: | 10.1021/acs.joc.9b02093 |
| Abstrakt: | A five-step total synthesis of Dysoxylum alkaloids has been achieved using a biomimetic approach from zanthoxylamide protoalkaloids. The synthesis featured a direct amidation and a Bischler-Napieralski reaction to form the dihydroisoquinoline ring, which was then subjected to a Noyori asymmetric transfer hydrogenation to establish the stereogenic center at C-1. Our synthetic sequence provides an important perspective on the biosynthetic origin of Dysoxylum alkaloids, since 6 natural alkaloids and 12 synthetic analogues were obtained with high enantioselectivity and in overall yields up to 68%. In addition, we describe the acute toxicity toward zebrafish embryos of Dysoxylum alkaloids, comparing their toxicity with that of their corresponding zanthoxylamide protoalkaloids and establishing an enantioselectivity-toxicity relationship. |
| Databáze: | MEDLINE |
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