Biomimetic Total Synthesis of Enterocin

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2021 Jul 19

PMID 34278701

Citations 4

Authors

Lilla Koser

Vivian Miles Lechner

Thorsten Bach

Affiliations

Soon will be listed here.

Abstract

The first chemical total synthesis of the highly oxygenated polyketide enterocin has been accomplished. The key step of the synthesis was a late-stage biomimetic reaction cascade involving two intramolecular aldol reactions in which each step proceeded in 52 % yield (averaged) and which established four of the seven stereogenic centers. The pivotal precursor for the cascade reaction was assembled from three readily available building blocks. A chiral dithioacetal with two stereogenic centers originating from L-arabinose represented the core fragment to both ends of which the other building blocks were attached by aldol reactions. The remaining stereogenic center was installed by Davis oxygenation immediately prior to the key step.

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Biomimetic Total Synthesis of Enterocin.

Koser L, Lechner V, Bach T Angew Chem Int Ed Engl. 2021; 60(37):20269-20273.

PMID: 34278701 PMC: 8457242. DOI: 10.1002/anie.202108157.

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