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Chemo‐enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)‐Epoxysorbicillinol
Author(s) -
Sib Anna,
Gulder Tobias A. M.
Publication year - 2018
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.201802176
Subject(s) - enantioselective synthesis , total synthesis , chemistry , enzyme , cytotoxicity , stereochemistry , combinatorial chemistry , nanotechnology , organic chemistry , biochemistry , in vitro , materials science , catalysis
The sorbicillinoids are a large family of fungal natural products, many of which possess highly challenging molecular architectures. Depending on their individual structures they exhibit strong biological activities ranging from radical scavenging and anti‐infective properties to cytotoxicity. Despite the resulting strong biomedical potential of these natural products and the interest of synthetic chemists owing to their fascinating structures, many sorbicillinoids are currently not synthetically accessible, thus hampering in‐depth biological characterization and structural diversification. By using recombinant oxidoreductase SorbC and readily accessible sorbicillin‐type synthetic precursors, we have developed enantioselective, one‐pot chemo‐enzymatic routes to a broad range of sorbicillinoids, thereby establishing total syntheses of oxosorbicillinol, sorrentanone, rezishanones B and C, sorbicatechol A, bisvertinolone, and (+)‐epoxysorbicillinol.