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Biomimetic Total Synthesis of Enterocin
Author(s) -
Koser Lilla,
Lechner Vivian Miles,
Bach Thorsten
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202108157
Subject(s) - stereocenter , aldol reaction , polyketide , intramolecular force , stereochemistry , yield (engineering) , chemistry , total synthesis , cascade , cascade reaction , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , biosynthesis , enzyme , metallurgy , chromatography
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.