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Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the... AbstractThe total synthesis of the natural phytoalexin 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one (3) isolated from Eichhornia crassipes was accomplished in seven steps. The synthetic strategy included a Friedel–Crafts acylation and a Jacobsen–Katsuki epoxidation as the key reactions to obtain the target compound. Based on a comparison of the NMR data and a crystal structure of 3, the previously proposed structure of 2,5-dimethoxy-4-phenyl-benzoindenone (2) isolated from the same plant has been revised. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Zeitschrift für Naturforschung B de Gruyter

Synthesis of 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one and structural revision of the benzoindenone from Eichhornia crassipes

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Publisher
de Gruyter
Copyright
©2019 Walter de Gruyter GmbH, Berlin/Boston
ISSN
0932-0776
eISSN
1865-7117
DOI
10.1515/znb-2018-0181
Publisher site
See Article on Publisher Site

Abstract

AbstractThe total synthesis of the natural phytoalexin 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one (3) isolated from Eichhornia crassipes was accomplished in seven steps. The synthetic strategy included a Friedel–Crafts acylation and a Jacobsen–Katsuki epoxidation as the key reactions to obtain the target compound. Based on a comparison of the NMR data and a crystal structure of 3, the previously proposed structure of 2,5-dimethoxy-4-phenyl-benzoindenone (2) isolated from the same plant has been revised.

Journal

Zeitschrift für Naturforschung B – de Gruyter

Published: Feb 25, 2019

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