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Synthesis and Determination of Absolute Configuration of Zealexin A1, a Sesquiterpenoid Phytoalexin from Zea mays
Author(s) -
Yajima Arata,
Shimura Mikaho,
Saito Tatsuo,
Katsuta Ryo,
Ishigami Ken,
Huffaker Alisa,
Schmelz Eric A.
Publication year - 2021
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.202001596
Subject(s) - chemistry , phytoalexin , absolute configuration , stereocenter , enantioselective synthesis , total synthesis , sesquiterpene , stereochemistry , natural product , stereoselectivity , monoterpene , zea mays , organic chemistry , catalysis , biochemistry , agronomy , biology , resveratrol
The enantioselective synthesis of zealexin A1, a sesquiterpene phytoalexin isolated from maize Zea mays is described for the first time. Our methodology for the total synthesis of zealexin A1 involved the stereoselective construction of the stereogenic center via enzymatic resolution followed by Johnson–Claisen rearrangement. The absolute configuration of the natural product was determined through gas chromatography analyses for the methyl esters for both synthetic and natural zealexin A1.