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Molecules 2016, 21(8), 1058; doi:10.3390/molecules21081058

Synthesis of Natural Homoisoflavonoids Having Either 5,7-Dihydroxy-6-methoxy or 7-Hydroxy-5,6-dimethoxy Groups

1
College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Korea
2
Department of Bioscience and Biotechnology, Sejong University, Seoul 05006, Korea
3
Departments of Ophthalmology, Eugene and Marilyn Glick Eye Institute, Biochemistry and Molecular Biology, and Pharmacology and Toxicology, Indiana University School of Medicine, Indianapolis, IN 46202, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 14 July 2016 / Revised: 8 August 2016 / Accepted: 9 August 2016 / Published: 13 August 2016
(This article belongs to the Special Issue Flavonoids: From Structure to Health Issues)
View Full-Text   |   Download PDF [1142 KB, uploaded 13 August 2016]   |  

Abstract

Naturally occurring homoisoflavonoids containing either 5,7-dihydroxy-6-methoxy or 7-hydroxy-5,6-dimethoxy groups such as the antiangiogenic homoisoflavanone, cremastranone, were synthesized via three or four linear steps from the known 4-chromenone. This facile synthesis includes chemoselective 1,4-reduction of 4-chromenone and selective deprotection of 3-benzylidene-4-chromanone a containing C7-benzyloxy group. View Full-Text
Keywords: homoisoflavanone; cremastranone; 4-chromanone; 4-chromenone 1,4-reduction homoisoflavanone; cremastranone; 4-chromanone; 4-chromenone 1,4-reduction
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MDPI and ACS Style

Lee, H.; Yuan, Y.; Rhee, I.; Corson, T.W.; Seo, S.-Y. Synthesis of Natural Homoisoflavonoids Having Either 5,7-Dihydroxy-6-methoxy or 7-Hydroxy-5,6-dimethoxy Groups. Molecules 2016, 21, 1058.

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