期刊
TETRAHEDRON LETTERS
卷 58, 期 47, 页码 4479-4482出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.10.038
关键词
Total synthesis; Xanthones; Spirochromanones; Asymmetric synthesis; Enzymatic resolution
资金
- GAKUIN TOKUBETSU KENKYUHI Grant (Musashino University)
We report the asymmetric total synthesis of (+)-blennolide C and (+)-gonytolide C isolated from endophytic fungi. The synthesis involved construction of a spirochromanone with a chiral quaternary carbon by the aldol reaction of o-hydroxyacetophenones and optically active alpha-oxygenated cyclohexenone, followed by cyclization under acidic conditions. Oxidative cleavage of the alkene moiety of the spirochromanone furnished the chromanone diester. Through treating the diester with a Lewis acid, the first total synthesis of (+)-blennolide C was achieved by deprotecting the oxygen functionality of the diester and simultaneous Dieckmann condensation. Total synthesis of (+)-gonytolide C was also achieved by lac tone formation from the deprotected diester. (C) 2017 Elsevier Ltd. All rights reserved.
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