Premium
A New Secondary Metabolite from Alternaria Alternata : Structure Elucidation and Total Synthesis of Altenuic Acid IV
Author(s) -
Kohler Dominik,
Podlech Joachim
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.201801801
Subject(s) - chemistry , total synthesis , alternaria alternata , metabolite , stereochemistry , muconic acid , diol , yield (engineering) , nuclear magnetic resonance spectroscopy , lactone , organic chemistry , biochemistry , botany , benzene , materials science , metallurgy , biology
A putative intermediate in the biosynthesis of altenuic acids I–III was isolated from Alternaria alternata in the 1950ies and a sample survived over the decades. This resorcylic lactone named altenuic acid IV is a composite of a resorcylic and a muconic acid. Its structure was confirmed by NMR spectroscopy and by total synthesis. Altenuic acid IV was here obtained starting with 2‐bromo‐4,6‐dimethoxybenzene and 4‐methylbenzene‐1,2‐diol with a total yield of 20 %. The synthesis was achieved in ten steps where the longest sequence consists of seven steps. Key steps were an oxidative ring opening of a bromocresol furnishing a bromomuconate and its Suzuki coupling with a resorcylate‐derived boronate.