Total Syntheses of Biologically Active Pterocarpan, Isoflavan, and Isoflavanone from Dalbergia oliveri

Dileep Kumar Singh, Jinwoo Kim, Jong Hyuk Sung, Ikyon Kim

Research output: Contribution to journalArticle

Abstract

Biological screening of the natural products from Dalbergia oliveri identified that (6aR,11aR)-3,8-dihydroxy-9-methoxypterocarpan and (3R)-7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone significantly increased the proliferation of dermal papilla cells and subcutaneous injection of these compounds induced the anagen of hair cycle in animal models. These interesting biological activities led us to design a practical synthetic route to these natural products for further pharmacological evaluation. Here we report the first total syntheses of naturally occurring pterocarpan ((6aR,11aR)-3,8-dihydroxy-9-methoxypterocarpan), isoflavan ((3R)-5′-methoxyvestitol), and isoflavanone ((3R)-7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone) in a racemic form. A mild ZnCl2-mediated [3 + 2] annulation method was utilized with chromenes and 2-methoxy-1,4-benzoquinone to construct a pterocarpan framework in a one-pot manner. O-methylation and reductive cleavage of the benzylic C─O bond afforded 5′-methoxyvestitol, which was transformed to isoflavanone, 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone, via a three-step sequence including DDQ-mediated benzylic oxidation.

Original languageEnglish
Pages (from-to)239-243
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume39
Issue number2
DOIs
Publication statusPublished - 2018 Feb

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Pterocarpans
Biological Products
Benzopyrans
Methylation
Carbon Monoxide
Bioactivity
Screening
Animals
Oxidation
isoflavanone

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Total Syntheses of Biologically Active Pterocarpan, Isoflavan, and Isoflavanone from Dalbergia oliveri",
abstract = "Biological screening of the natural products from Dalbergia oliveri identified that (6aR,11aR)-3,8-dihydroxy-9-methoxypterocarpan and (3R)-7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone significantly increased the proliferation of dermal papilla cells and subcutaneous injection of these compounds induced the anagen of hair cycle in animal models. These interesting biological activities led us to design a practical synthetic route to these natural products for further pharmacological evaluation. Here we report the first total syntheses of naturally occurring pterocarpan ((6aR,11aR)-3,8-dihydroxy-9-methoxypterocarpan), isoflavan ((3R)-5′-methoxyvestitol), and isoflavanone ((3R)-7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone) in a racemic form. A mild ZnCl2-mediated [3 + 2] annulation method was utilized with chromenes and 2-methoxy-1,4-benzoquinone to construct a pterocarpan framework in a one-pot manner. O-methylation and reductive cleavage of the benzylic C─O bond afforded 5′-methoxyvestitol, which was transformed to isoflavanone, 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone, via a three-step sequence including DDQ-mediated benzylic oxidation.",
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Total Syntheses of Biologically Active Pterocarpan, Isoflavan, and Isoflavanone from Dalbergia oliveri. / Singh, Dileep Kumar; Kim, Jinwoo; Sung, Jong Hyuk; Kim, Ikyon.

In: Bulletin of the Korean Chemical Society, Vol. 39, No. 2, 02.2018, p. 239-243.

Research output: Contribution to journalArticle

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