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A Straightforward Synthesis of Polyketides via Ester Dienolate Matteson Homologation.

ABSTRACT: Application of ester dienolates as nucleophiles in Matteson homologations allows for the stereoselective synthesis of highly substituted ?,?-unsaturated ?-hydroxy carboxyl acids, structural motifs widespread found in polyketide natural products. The protocol is rather flexible and permits the introduction of substituents and functionalities also at those positions which are not accessible by the commonly used aldol reaction. Therefore, this ester dienolate Matteson approach is an interesting alternative to the "classical" polyketide syntheses.

SUBMITTER: Andler O

PROVIDER: S-EPMC7839490 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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A Straightforward Synthesis of Polyketides via Ester Dienolate Matteson Homologation.

Andler Oliver O Kazmaier Uli U

Chemistry (Weinheim an der Bergstrasse, Germany) 20201215 3

Application of ester dienolates as nucleophiles in Matteson homologations allows for the stereoselective synthesis of highly substituted α,β-unsaturated δ-hydroxy carboxyl acids, structural motifs widespread found in polyketide natural products. The protocol is rather flexible and permits the introduction of substituents and functionalities also at those positions which are not accessible by the commonly used aldol reaction. Therefore, this ester dienolate Matteson approach is an interesting alt ...[more]

PMID: 33089903

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