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Catalytic asymmetric formal synthesis of beraprost.

ABSTRACT: The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an ?,?-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C-C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C-H insertion and the subsequent reduction from the convex face.

SUBMITTER: Kobayashi Y 

PROVIDER: S-EPMC4685892 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Catalytic asymmetric formal synthesis of beraprost.

Kobayashi Yusuke Y   Kuramoto Ryuta R   Takemoto Yoshiji Y  

Beilstein journal of organic chemistry 20151218

The first catalytic asymmetric synthesis of the key intermediate for beraprost has been achieved through an enantioselective intramolecular oxa-Michael reaction of an α,β-unsaturated amide mediated by a newly developed benzothiadiazine catalyst. The Weinreb amide moiety and bromo substituent of the Michael adduct were utilized for the C-C bond formations to construct the scaffold. All four contiguous stereocenters of the tricyclic core were controlled via Rh-catalyzed stereoselective C-H inserti  ...[more]

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