title: Synthesis of Natural Homoisoflavonoids Having Either 5,7-Dihydroxy-6-methoxy or 7-Hydroxy-5,6-dimethoxy Groups.
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.
authors.affiliation: College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Korea. a13079@naver.com.
authors.forename: Hyungjun
authors.initials: H
authors.lastname: Lee
authors.affiliation: College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Korea. wonwol@gmail.com.
authors.forename: Yue
authors.initials: Y
authors.lastname: Yuan
authors.affiliation: Department of Bioscience and Biotechnology, Sejong University, Seoul 05006, Korea. nature@sejong.ac.kr.
authors.forename: Inmoo
authors.initials: I
authors.lastname: Rhee
authors.affiliation: 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. tcorson@iu.edu.
authors.forename: Timothy W
authors.initials: TW
authors.lastname: Corson
authors.affiliation: College of Pharmacy and Gachon Institute of Pharmaceutical Sciences, Gachon University, Incheon 21936, Korea. syseo@gachon.ac.kr.
authors.forename: Seung-Yong
authors.initials: SY
authors.lastname: Seo
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: C524883:5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-6-methoxychroman-4-one; D001688:Biological Products; D007529:Isoflavones
keywords: 4-chromanone; 4-chromenone 1,4-reduction; cremastranone; homoisoflavanone