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

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...

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Autores principales: Lee, Sangki, Yang, Jewon, Yang, Sehun, Lee, Geumwoo, Oh, Daehyun, Ha, Min Woo, Hong, Suckchang, Park, Hyeung-geun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7690313/
https://www.ncbi.nlm.nih.gov/pubmed/33282828
http://dx.doi.org/10.3389/fchem.2020.577371
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author Lee, Sangki
Yang, Jewon
Yang, Sehun
Lee, Geumwoo
Oh, Daehyun
Ha, Min Woo
Hong, Suckchang
Park, Hyeung-geun
author_facet Lee, Sangki
Yang, Jewon
Yang, Sehun
Lee, Geumwoo
Oh, Daehyun
Ha, Min Woo
Hong, Suckchang
Park, Hyeung-geun
author_sort Lee, Sangki
collection PubMed
description 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.
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spelling pubmed-76903132020-12-04 Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate Lee, Sangki Yang, Jewon Yang, Sehun Lee, Geumwoo Oh, Daehyun Ha, Min Woo Hong, Suckchang Park, Hyeung-geun Front Chem Chemistry 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. Frontiers Media S.A. 2020-11-12 /pmc/articles/PMC7690313/ /pubmed/33282828 http://dx.doi.org/10.3389/fchem.2020.577371 Text en Copyright © 2020 Lee, Yang, Yang, Lee, Oh, Ha, Hong and Park. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Lee, Sangki
Yang, Jewon
Yang, Sehun
Lee, Geumwoo
Oh, Daehyun
Ha, Min Woo
Hong, Suckchang
Park, Hyeung-geun
Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate
title Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate
title_full Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate
title_fullStr Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate
title_full_unstemmed Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate
title_short Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate
title_sort enantioselective synthesis of (+)-coerulescine by a phase-transfer catalytic allylation of diphenylmethyl tert-butyl α-(2-nitrophenyl)malonate
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7690313/
https://www.ncbi.nlm.nih.gov/pubmed/33282828
http://dx.doi.org/10.3389/fchem.2020.577371
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