Model studies of (+)-bergenin: A convenient formation of aryl δ-lactones

Hua, Xiao-Gang; Mague, Joel T.; Li, Chao‐Jun

doi:10.1016/s0040-4039(98)01488-9

Cited by 19 publications

(6 citation statements)

References 38 publications

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“…In addition, glyceraldehyde, which contains a free hydroxy group, can be directly used to give the target product in 63% yield. This convenient method for the synthesis of allenyl δ-lactone potentially provides a basis for the construction of Bergenin and related compounds …”

Section: Propargylindium and Allenylindium Reagentmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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allylation performed in aqueous media, an efficient synthesis of highly functionalized lactones was realized in good yields (64− 77%, Scheme 29). 238 However, the chirality installed during the first step almost had no influence on the second step, thus resulting in poor diastereoselectivity in the subsequent allylation reaction (1:1−2:1 dr).In situ formation of aldehyde from the oxidation of alcohol followed by one-pot indium-mediated allylation also provides an alternative method for the synthesis of homoallylic alcohol. Recently, Yadav and co-workers developed such a one-pot sequence by using chloramines-T (sodium salt of Nchlorotosylamide) as oxidant in the presence of a catalytic amount of FeCl 3 in CH 2 Cl 2 , giving rise to homoallylic alcohols in good to excellent yields (Scheme 30). 239 It is noteworthy that the generated byproduct of TsNH 2 (from the reduction of chloramines-T) may react with the in situ-formed aldehydes to give intermediates of N-tosylimines in the presence of 4 Å molecular sieve under refluxing; the thus-formed N-tosylimines subsequently underwent one-pot indium-mediated allylation to produce homoallylic amines in 60−80% yields. Later, a similar one-pot, two-step sequence for the synthesis of homoallylic alcohols via a galactose oxidase-mediated chemo-enzymatic oxidation of benzyl and cinnamyl alcohols to the corresponding Scheme 23 Scheme 24 Scheme 25 Scheme 26 Scheme 27 Scheme 28 Scheme 29 Scheme 30 Chemical Reviews Review dx.

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Section: Propargylindium and Allenylindium Reagentmentioning

confidence: 99%

Organoindium Reagents: The Preparation and Application in Organic Synthesis

et al. 2012

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“…It was suggested that the galloyl moiety is attached at C-11 since the two proton signals at d = 4.68 and 4.32 assigned to protons at C-11 were shifted to lower field than the corresponding protons in bergenin. Analysis of the 1 H-13 C COSY and HMBC experiments and comparison to the values published for bergenin [1], [2], [3] (spectral data), [4], [5] (X-ray analysis and stereochemistry) and 11-O-galloylbergenin [2], [3], [6] led to the identification of compound 1 as 11-O-(4¢-O-methylgalloyl)-bergenin, a new compound ( Fig. 1).…”

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confidence: 99%

Anti-Platelet Aggregating and Anti-Oxidative Activities of 11-O-(4′-O-Methylgalloyl)-bergenin, a New Compound Isolated fromCrassulacv. ‘Himaturi’

et al. 2005

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A new compound, 11- O-(4'- O-methylgalloyl)-bergenin was isolated from the MeOH extract of Crassula cv. 'Himaturi'. The structure of the compound was determined on the basis of chemical and spectroscopic data. It inhibited arachidonic acid-induced platelet aggregation more efficiently than acetylsalicylic acid and showed an anti-oxidative effect (EC (50) = 23.9 microM) equivalent to that of L-ascorbic acid or quercetin.

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“…Thereafter for about four decades, not much work has been done on bergenin except some reports on its isolation from the plant sources. Some attempts to prepare bergenin (1) were not successful [232,233]. Bergenin has gained much attention from the beginning of 21st century, as its pharmacological properties were gradually explored.…”

Section: Total Synthesismentioning

confidence: 99%

Diversity, pharmacology and synthesis of bergenin and its derivatives: Potential materials for therapeutic usages

Bajracharya

2015

Fitoterapia

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Model studies of (+)-bergenin: A convenient formation of aryl δ-lactones

Cited by 19 publications

References 38 publications

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Organoindium Reagents: The Preparation and Application in Organic Synthesis

Anti-Platelet Aggregating and Anti-Oxidative Activities of 11-O-(4′-O-Methylgalloyl)-bergenin, a New Compound Isolated fromCrassulacv. ‘Himaturi’

Diversity, pharmacology and synthesis of bergenin and its derivatives: Potential materials for therapeutic usages

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