Synthesis of homoisoflavanones—II

Farkas, L.; Gottsegen, Á.; Nógrádi, Mihäly; Strelisky, J.

doi:10.1016/s0040-4020(01)98209-2

Cited by 48 publications

(21 citation statements)

References 12 publications

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“…This synthesis is an alternative to the previously reported method for the synthesis of homoisoflavanones [7]. An attempt to obtain compound 3 by selective demethylation of intermediate 10, followed by reduction of the C¼C bond, failed.…”

mentioning

confidence: 88%

Taste‐Active Compounds in a Traditional Italian Food: ‘Lampascioni’

Borgonovo¹,

Caimi²,

Morini³

et al. 2008

Chemistry & Biodiversity

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Nature is a rich source of taste-active compounds, in particular of plant origin, many of which have unusual tastes. Many of these are found in traditional food, where spontaneous plants are used as ingredients. Some taste-active compounds were identified in the bulbs of Muscari comosum, a spontaneous plant belonging to the family of the Liliaceae, very common in the Mediterranean area, and used in traditional gastronomy (called 'lampascioni' in South Italy). The bulbs were extracted with a series of solvents of different polarity. The different fractions were submitted to a preliminary sensory evaluation, and the most interesting ones, characterized by a strong bitter taste and some chemestetic properties, were submitted to further purification and structural analysis. From the ethereal extract, several 3-benzyl-4-chromanones and one stilbene derivative were isolated. Pure compounds were examined for their taste activity by means of sensory evaluation, and proved to be responsible for the characteristic taste of this food. Some of these compounds have been synthesized de novo to confirm their structure.

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mentioning

confidence: 88%

Taste‐Active Compounds in a Traditional Italian Food: ‘Lampascioni’

Borgonovo¹,

Caimi²,

Morini³

et al. 2008

Chemistry & Biodiversity

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“…Dimethyldioxirane (DMD, as 0.05-0.1 M acetone solution) was prepared as described [12] and its peroxide content was determined iodometrically. Curox (potassium monopersulfate), the triple salt 2KHSO 5 .KHSO 4 .K 2 SO 4 , was used as received, a generous gift from the Peroxid-Chemie GmbH (München, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…For the synthesis of these oxygen-heterocyclic compounds, various procedures have been worked out. Homoisoflavones were synthesized by the ring closure of 2'-hydroxydihydrochalcones first by Farkas et al [4] and later in other laboratories [5][6][7][8]. A simple and convenient procedure is based on the exocyclic-endocyclic double bond migration of 3-arylmethylene-4-chromanones.…”

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confidence: 99%

Epoxidation of homoisoflavones

Lévai

2003

Journal of Heterocyclic Chem

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A comparative study of the epoxidation of homoisoflavones (3‐benzyl‐4‐chromones) 1–4 has been performed by various oxidizing agents, víz. Epoxidation with isolated dimethyldioxirane (Method A), with alkaline hydrogen peroxide (Method B), and with sodium hypochlorite (Method C) to obtain the epoxides 4–8. Compounds 2 and 3 have also been oxidized with a combination of dimethyldioxirane and Jacobsen's Mn(III)salen catalysts (R,R)‐11 and (S,S)‐11 to afford 3‐benzoyl‐4‐chromones 9 and 10. Structures of all new compounds have been elucidated by microanalyses, ir and nmr spectroscopic measurements.

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“…Farkas et al [171][172][173] accomplished the reaction of the appropriate ketone and aldehyde in hot acetic anhydride, which is a very simple and convenient method, but sometimes it requires a prolonged (e.g. 80 h) refluxing.…”

Section: Scheme 12mentioning

confidence: 99%

Synthesis of exocyclic α,β-unsaturated ketones

Lévai

2003

Arkivoc

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This review describes synthetic procedures for the preparation of selected groups of the most important exocyclic α,β-unsaturated ketones. Some of these α,β-enones, víz. aurones and 3-benzylidene-4-chromanones belong to the natural products. The others are synthetic substances which are convenient and especially important intermediates for the stereoselective synthesis of polycyclic ring systems. To illustrate the utility of any special procedures, relevant examples have been included. However, it is not the aim of the present review article to list and evaluate all the papers published in this field. Owing to the huge number of papers, such a goal would be an almost unrealizable task.

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Synthesis of homoisoflavanones—II

Cited by 48 publications

References 12 publications

Taste‐Active Compounds in a Traditional Italian Food: ‘Lampascioni’

Taste‐Active Compounds in a Traditional Italian Food: ‘Lampascioni’

Epoxidation of homoisoflavones

Synthesis of exocyclic α,β-unsaturated ketones

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