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Synthesis and Configuration of a p ‐Aminoacetophenonic Acid Isolated from Endophyte of the Mangrove Plant Kandel candel
Author(s) -
Xiong Xin,
Wu Yikang,
Liu Bo
Publication year - 2020
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.202000837
Subject(s) - chemistry , stereocenter , diastereomer , stereochemistry , enantioselective synthesis , natural product , reagent , aldol condensation , endophyte , column chromatography , aldol reaction , organic chemistry , catalysis , botany , biology
Two diastereomers of the title compound were synthesized through an enantioselective route, with the stereogenic center at the C‐2 derived from a commercially available reagent and the one at the C‐4 installed via Evans asymmetric aldol condensation. By comparison of 1 H and 13 C NMR spectra as well as optical rotation, the configuration of the natural product was as assigned as (‐2 R ,4 R ). Some interesting issues such as suppression of the undesired yet dominating formation of cyclic ethers associated with deprotection of a TBS protected terminal hydroxyl group and the previously unknown differences in 1 H NMR and IR between the end product separated by normal phase chromatography and that by reverse phase chromatography are also presented.