AUTHOR=Lee Sangki , Yang Jewon , Yang Sehun , Lee Geumwoo , Oh Daehyun , Ha Min Woo , Hong Suckchang , Park Hyeung-geun 

TITLE=Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate

JOURNAL=Frontiers in Chemistry

VOLUME=8

YEAR=2020

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2020.577371

DOI=10.3389/fchem.2020.577371

ISSN=2296-2646

ABSTRACT=<p>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, &gt;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.</p>