通过二苯基甲基 - 丁基α-(2-硝基苯基)丙二酸酯的相转移催化烯丙基化反应对(+)-异长春花胺进行对映选择性合成。
Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl -Butyl α-(2-Nitrophenyl)Malonate.
作者信息
Lee Sangki, Yang Jewon, Yang Sehun, Lee Geumwoo, Oh Daehyun, Ha Min Woo, Hong Suckchang, Park Hyeung-Geun
机构信息
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South Korea.
College of Pharmacy, Jeju National University, Jeju, South Korea.
出版信息
Front Chem. 2020 Nov 12;8:577371. doi: 10.3389/fchem.2020.577371. eCollection 2020.
A 7-step enantioselective synthetic method for preparing (S)(+)-coerulescine is reported through the use of diphenylmethyl tert-butyl α-(2-nitrophenyl)malonate (16% overall yield, >99% ee). Allylation is the key step under phase-transfer catalytic conditions (86% ee). This synthetic method can be used as a practical route for the synthesis of various derivatives of (S)(+)-coerulescine for analyzing its structure-activity relationships against its biological activities.
报道了一种通过使用二苯基甲基叔丁基α-(2-硝基苯基)丙二酸酯制备(S)(+)-蓝堇西定的7步对映选择性合成方法（总产率16%，对映体过量>99%）。烯丙基化是相转移催化条件下的关键步骤（对映体过量86%）。该合成方法可作为合成(S)(+)-蓝堇西定各种衍生物的实用路线，用于分析其结构-活性关系及其生物活性。
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