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An efficient synthesis of 9‐anthrone lactone derivatives via the Knoevenagel condensation and intramolecular cyclization
Author(s) -
Tan Weiqiang,
Zheng Jifang,
Guan Jing,
Zhan Xiuzhi,
Gao Liming,
Lyu Lili,
Shan Bin,
Yang Qipeng,
Ma Mingliang,
Xia Yan
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3785
Subject(s) - chemistry , knoevenagel condensation , intramolecular force , anthrone , lactone , natural product , condensation , intramolecular reaction , condensation reaction , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , computational chemistry , catalysis , physics , thermodynamics
One‐step synthesis of 9‐anthrone lactone derivatives from 1‐acetyloxyanthraquinone with a variety of dicarbonyl substrates in the presence of K 2 CO 3 by Knovenagel condensation and intramolecular cyclization is developed. Possible reaction mechanisms have been investigated using the density functional theory (DFT), which has been widely used in the study of reaction mechanism. The strategy could be useful for the synthesis of the core structure of marine natural product aspergiolide.