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Simple and efficient synthesis of bicyclic enol-carbamates: access to brabantamides and their analogues.

ABSTRACT: A novel synthetic approach towards the formation of the unusual bicyclic enol-carbamates, as found in brabantamides A-C, is reported. The bicyclic oxazolidinone framework was obtained in very good yield and with high E/Z selectivity from a readily available β-ketoester under mild reaction conditions using Tf₂O and 2-chloropyridine tandem. The major E isomer was used in the synthesis of the brabantamide A analogue.

SUBMITTER: Zaborsky O

PROVIDER: S-EPMC9049743 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Simple and efficient synthesis of bicyclic enol-carbamates: access to brabantamides and their analogues.

Záborský Ondrej O Petrovičová Ľudmila Ľ Doháňošová Jana J Moncol Ján J Fischer Róbert R

RSC advances 20200213 12

A novel synthetic approach towards the formation of the unusual bicyclic enol-carbamates, as found in brabantamides A-C, is reported. The bicyclic oxazolidinone framework was obtained in very good yield and with high E/Z selectivity from a readily available β-ketoester under mild reaction conditions using Tf2O and 2-chloropyridine tandem. The major E isomer was used in the synthesis of the brabantamide A analogue. ...[more]

PMID: 35493865

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