Total Synthesis of Anmindenol A and Its Application to the Design, Synthesis, and Biological Evaluation of Derivatives Thereof

The first total synthesis of anmindenol A is described in four steps. A notable feature of the synthetic route includes the efficient construction of the 3,10-dialkylsubstituted benzofulvene core via a stereoselective vinylogous Stork enamine aldol condensation. The strategy provided a blueprint for...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-09, Vol.84 (17), p.10953-10961
Main Authors: Jo, Jeyun, Jeong, Myeonggyo, Ahn, Ji-Su, Akter, Jinia, Kim, Hyung-Sik, Suh, Young-Ger, Yun, Hwayoung
Format: Article
Language:English
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Summary:The first total synthesis of anmindenol A is described in four steps. A notable feature of the synthetic route includes the efficient construction of the 3,10-dialkylsubstituted benzofulvene core via a stereoselective vinylogous Stork enamine aldol condensation. The strategy provided a blueprint for the practical preparation of derivatives with modifications in the C-10 alkyl substituents. The novel derivatives inhibited nitric oxide production in stimulated RAW 264.7 macrophage cells.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01564