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Total Synthesis of Luminmycin A, a Cryptic Natural Product from Photorhabdus Luminescens
Author(s) -
Servatius Phil,
Stach Tanja,
Kazmaier Uli
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900460
Subject(s) - photorhabdus luminescens , natural product , isomerization , photorhabdus , chemistry , gene cluster , stereochemistry , fatty acid , intramolecular force , ring (chemistry) , gene , biochemistry , organic chemistry , catalysis
Luminmycin A, a natural proteasome inhibitor transcripted by a silent gene cluster from Photorhabdus luminescens , belongs to the compound family of the syrbactins and is structurally closely related to the glidobactins. Key step for the synthesis of the 12‐membered cyclopeptide ring is an intramolecular Horner–Wadsworth–Emmons reaction, while the double unsaturated fatty acid side chain can be obtained via phosphane‐catalyzed isomerization of a corresponding acetylenic fatty acid ester.