Synthesis of the natural isoflavanones ferreirin, dalbergioidin, and ougenin

L. Farkas, Á Gottsegen, M. Nógrádi, S. Antus

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

2′-Benzoyloxy-7-benzyloxy-4′,5-dimethoxy-2- methoxycarbonylisoflavone (12), prepared in nine steps by established methods, has been degraded to the corresponding phenyl benzyl ketone (9), which cyclises on treatment with ethyl formate and sodium to give 7-benzyloxy-2′-hydroxy- 4′5-dimethoxyisoflavone (15); the latter has been converted in four steps into 2′,5,7-trihydroxy-4′-methoxyisoflavanone (1), identical with natural ferreirin. (±)-Dalbergioidin has been prepared by hydrogenation and subsequent saponification of 2′,4′,5,7-tetra-acetoxyisoflavone. 3-Methyl-2,4,6-trihydroxyphenyl 2,4-dimethoxybenzyl ketone (21), when treated with ethoxalyl chloride, gives mainly 2-ethoxycarbonyl-5,7-dihydroxy-2′, 4′-dimethoxy-6-methylisoflavone (23), which has been transformed in six steps into (±)-2′,4′,5-trihydroxy-7-methoxy-6- methylisolfavanone, (±)-ougenin (20).

Original languageEnglish
Pages (from-to)1994-2000
Number of pages7
JournalJournal of the Chemical Society C: Organic
DOIs
Publication statusPublished - 1971

Fingerprint

Ketones
Saponification
Hydrogenation
Sodium
dalbergioidin
isoflavanone
ethyl formate
ethoxalyl chloride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of the natural isoflavanones ferreirin, dalbergioidin, and ougenin. / Farkas, L.; Gottsegen, Á; Nógrádi, M.; Antus, S.

In: Journal of the Chemical Society C: Organic, 1971, p. 1994-2000.

Research output: Contribution to journalArticle

@article{52a605bca8384872826ef5f84e9e94d9,
title = "Synthesis of the natural isoflavanones ferreirin, dalbergioidin, and ougenin",
abstract = "2′-Benzoyloxy-7-benzyloxy-4′,5-dimethoxy-2- methoxycarbonylisoflavone (12), prepared in nine steps by established methods, has been degraded to the corresponding phenyl benzyl ketone (9), which cyclises on treatment with ethyl formate and sodium to give 7-benzyloxy-2′-hydroxy- 4′5-dimethoxyisoflavone (15); the latter has been converted in four steps into 2′,5,7-trihydroxy-4′-methoxyisoflavanone (1), identical with natural ferreirin. (±)-Dalbergioidin has been prepared by hydrogenation and subsequent saponification of 2′,4′,5,7-tetra-acetoxyisoflavone. 3-Methyl-2,4,6-trihydroxyphenyl 2,4-dimethoxybenzyl ketone (21), when treated with ethoxalyl chloride, gives mainly 2-ethoxycarbonyl-5,7-dihydroxy-2′, 4′-dimethoxy-6-methylisoflavone (23), which has been transformed in six steps into (±)-2′,4′,5-trihydroxy-7-methoxy-6- methylisolfavanone, (±)-ougenin (20).",
author = "L. Farkas and {\'A} Gottsegen and M. N{\'o}gr{\'a}di and S. Antus",
year = "1971",
doi = "10.1039/J39710001994",
language = "English",
pages = "1994--2000",
journal = "Journal of the Chemical Society C: Organic Chemistry",
issn = "0022-4952",
publisher = "Chemical Society",

}

TY - JOUR

T1 - Synthesis of the natural isoflavanones ferreirin, dalbergioidin, and ougenin

AU - Farkas, L.

AU - Gottsegen, Á

AU - Nógrádi, M.

AU - Antus, S.

PY - 1971

Y1 - 1971

N2 - 2′-Benzoyloxy-7-benzyloxy-4′,5-dimethoxy-2- methoxycarbonylisoflavone (12), prepared in nine steps by established methods, has been degraded to the corresponding phenyl benzyl ketone (9), which cyclises on treatment with ethyl formate and sodium to give 7-benzyloxy-2′-hydroxy- 4′5-dimethoxyisoflavone (15); the latter has been converted in four steps into 2′,5,7-trihydroxy-4′-methoxyisoflavanone (1), identical with natural ferreirin. (±)-Dalbergioidin has been prepared by hydrogenation and subsequent saponification of 2′,4′,5,7-tetra-acetoxyisoflavone. 3-Methyl-2,4,6-trihydroxyphenyl 2,4-dimethoxybenzyl ketone (21), when treated with ethoxalyl chloride, gives mainly 2-ethoxycarbonyl-5,7-dihydroxy-2′, 4′-dimethoxy-6-methylisoflavone (23), which has been transformed in six steps into (±)-2′,4′,5-trihydroxy-7-methoxy-6- methylisolfavanone, (±)-ougenin (20).

AB - 2′-Benzoyloxy-7-benzyloxy-4′,5-dimethoxy-2- methoxycarbonylisoflavone (12), prepared in nine steps by established methods, has been degraded to the corresponding phenyl benzyl ketone (9), which cyclises on treatment with ethyl formate and sodium to give 7-benzyloxy-2′-hydroxy- 4′5-dimethoxyisoflavone (15); the latter has been converted in four steps into 2′,5,7-trihydroxy-4′-methoxyisoflavanone (1), identical with natural ferreirin. (±)-Dalbergioidin has been prepared by hydrogenation and subsequent saponification of 2′,4′,5,7-tetra-acetoxyisoflavone. 3-Methyl-2,4,6-trihydroxyphenyl 2,4-dimethoxybenzyl ketone (21), when treated with ethoxalyl chloride, gives mainly 2-ethoxycarbonyl-5,7-dihydroxy-2′, 4′-dimethoxy-6-methylisoflavone (23), which has been transformed in six steps into (±)-2′,4′,5-trihydroxy-7-methoxy-6- methylisolfavanone, (±)-ougenin (20).

UR - http://www.scopus.com/inward/record.url?scp=36148940469&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=36148940469&partnerID=8YFLogxK

U2 - 10.1039/J39710001994

DO - 10.1039/J39710001994

M3 - Article

SP - 1994

EP - 2000

JO - Journal of the Chemical Society C: Organic Chemistry

JF - Journal of the Chemical Society C: Organic Chemistry

SN - 0022-4952

ER -