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

ABSTRACT: A 7-step enantioselective synthetic method for preparing (S)(+)-coerulescine is reported through the use of diphenylmethyl tert-butyl ?-(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.

SUBMITTER: Lee S

PROVIDER: S-EPMC7690313 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Lee Sangki S Yang Jewon J Yang Sehun S Lee Geumwoo G Oh Daehyun D Ha Min Woo MW Hong Suckchang S Park Hyeung-Geun HG

Frontiers in chemistry 20201112

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. ...[more]

PMID: 33282828

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