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通过生物启发方法合成阿替生、阿里西丁、去氢吴茱萸碱和吴茱萸次碱二萜生物碱。

Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach.

机构信息

Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy and State Key Laboratory of Biotherapy, Sichuan University, Chengdu, 610041, P.R. China.

出版信息

Angew Chem Int Ed Engl. 2016 Dec 12;55(50):15667-15671. doi: 10.1002/anie.201609882. Epub 2016 Nov 17.

Abstract

A unified approach to four different (atisine, ajaconine, denudatine, and hetidine) diterpenoid alkaloid skeletons was developed and applied to the total synthesis of the natural products dihydroajaconine (2, atisine type) and gymnandine (4, denudatine type). The synthesis features a biogenetically inspired strategy that relies on C-H oxidation, aza-pinacol coupling, and aza-Prins cyclization as key steps.

摘要

开发了一种统一的方法来处理四种不同的(阿替生碱、阿枯米定碱、去氢吴茱萸碱和替啶碱)二萜生物碱骨架,并将其应用于天然产物二氢吴茱萸碱(2,阿替生碱型)和 Gymnandine(4,去氢吴茱萸碱型)的全合成。该合成的特点是一种受生物启发的策略,依赖于 C-H 氧化、氮杂-频哪醇偶联和氮杂-Prins 环化作为关键步骤。

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