Synthesis of natural homoisoflavonoids having either 5,7-dihydroxy-6-methoxy or 7-hydroxy-5,6-dimethoxy groups

Hyungjun Lee, Yue Yuan, Inmoo Rhee, Timothy Corson, Seung Yong Seo

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish (US)
Article number1058
JournalMolecules
Volume21
Issue number8
DOIs
StatePublished - Aug 1 2016

Fingerprint

Isoflavones
synthesis
5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-6-methoxychroman-4-one

Keywords

  • 4-Chromanone
  • 4-Chromenone 1,4-reduction
  • Cremastranone
  • Homoisoflavanone

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of natural homoisoflavonoids having either 5,7-dihydroxy-6-methoxy or 7-hydroxy-5,6-dimethoxy groups. / Lee, Hyungjun; Yuan, Yue; Rhee, Inmoo; Corson, Timothy; Seo, Seung Yong.

In: Molecules, Vol. 21, No. 8, 1058, 01.08.2016.

Research output: Contribution to journalArticle

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AU - Yuan, Yue

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AU - Corson, Timothy

AU - Seo, Seung Yong

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AB - 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.

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