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 ca...
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| Format: | Article |
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Frontiers Media S.A.
2020-11-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2020.577371/full |
| _version_ | 1818114989163020288 |
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| author | Sangki Lee Jewon Yang Sehun Yang Geumwoo Lee Daehyun Oh Min Woo Ha Suckchang Hong Hyeung-geun Park |
| author_facet | Sangki Lee Jewon Yang Sehun Yang Geumwoo Lee Daehyun Oh Min Woo Ha Suckchang Hong Hyeung-geun Park |
| author_sort | Sangki Lee |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-11T03:59:29Z |
| format | Article |
| id | doaj.art-eedb60bd067847528faf81b2a16b0d38 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-11T03:59:29Z |
| publishDate | 2020-11-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-eedb60bd067847528faf81b2a16b0d382022-12-22T01:21:41ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-11-01810.3389/fchem.2020.577371577371Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)MalonateSangki Lee0Jewon Yang1Sehun Yang2Geumwoo Lee3Daehyun Oh4Min Woo Ha5Suckchang Hong6Hyeung-geun Park7Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaCollege of Pharmacy, Jeju National University, Jeju, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaResearch Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul, South KoreaA 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.https://www.frontiersin.org/articles/10.3389/fchem.2020.577371/fullcoerulescineenantioselectivesynthesisphase-transfer catalysisalkylation |
| spellingShingle | Sangki Lee Jewon Yang Sehun Yang Geumwoo Lee Daehyun Oh Min Woo Ha Suckchang Hong Hyeung-geun Park Enantioselective Synthesis of (+)-Coerulescine by a Phase-Transfer Catalytic Allylation of Diphenylmethyl tert-Butyl α-(2-Nitrophenyl)Malonate Frontiers in Chemistry coerulescine enantioselective synthesis phase-transfer catalysis alkylation |
| 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 | coerulescine enantioselective synthesis phase-transfer catalysis alkylation |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2020.577371/full |
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