Efficient synthesis of baicalin and its analogs

Li, Yangfeng; Yu, Biao; Sun, Jiansong; Wang, Renxiao

doi:10.1016/j.tetlet.2015.04.083

Cited by 16 publications

(12 citation statements)

References 35 publications

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“…Thus, p ‐methoxyphenyl galactoside 11 , prepared from d ‐galactose in four steps in 70 % overall yield, was subjected to benzoylation conditions to give 12 (95 %). To convert the acid‐sensitive 12 into the corresponding galactosyl bromide 13 , a two‐step sequence of de‐ p ‐methoxyphenylation and PPh 3 /CBr 4 ‐mediated bromination was adopted; the desired bromide was obtained in 58 % yield (over two steps). The synthesis of arabinosyl ortho ‐alkynylbenzoate 21 began with bromide 14 , which was transformed into allyl orthoester 15 to selectively block the 1,2‐OH groups (89 %).…”

Section: Resultsmentioning

confidence: 99%

First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B

Liu¹,

Hu²,

Liu³

et al. 2017

Eur J Org Chem

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Based on the application of phase‐transfer‐catalysis and Yu glycosylations, the first total syntheses of the arylnaphthyl glycosides phyllanthusmin D and 4′′‐O‐acetylmananthoside B, which have been claimed to be ideal antitumoral lead compounds in terms of cytotoxicity, cytotoxic selectivity, and a new mechanism of action, were achieved. Starting from easily accessible compounds, the two target molecules were obtained with longest linear sequences of 9 and 15 steps, in overall yields of 29 and 9 %, respectively. As part of this synthetic investigation, an efficient and scalable synthetic route to diphyllin was established, and the atropisomeric phenomenon in the arylnaphthyl glycosides was also confirmed.

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Section: Resultsmentioning

confidence: 99%

First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B

Liu¹,

Hu²,

Liu³

et al. 2017

Eur J Org Chem

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“…Considering the foreseeable challenges in glycosylation of the phenolic aglycone, we decided to introduce a monosaccharide unit [56] Botting et al, 2008; [57] Yang & Dai et al, 2016; [58] etc. [71] Brodbelt et al, 2013; [72] Wang & Sun et al, 2015 [73]…”

Section: Synthesis Of Cassiasides C and C2 (75 And 74)mentioning

confidence: 99%

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Zhu

2018

Chin. J. Chem.

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Traditional Chinese medicine (TCM) is a huge treasure trove for the discovery and development of modern pharmaceuticals. Indeed, numerous biologically and pharmacologically significant molecules have been identified from TCM; among them, a considerable portion belongs to glycosides. These glycosides are extremely diverse in structures, consisting of a large variety of aglycones, glycans, as well as glycosidic linkages. In addition, these glycosides occur frequently as a complicated mixture of congeners in the nature sources. This micro‐heterogeneity leads to the isolation of a homogeneous glycoside in an appreciable amount a formidable task. Therefore, development of synthetic approaches toward these nature glycosides has received great attention. In this account, we summarize our twenty‐year efforts spent on this topic. Fifty five representative TCM‐relevant glycosides synthesized by our group are highlighted. Based on the aglycone structure, these glycosides are categorized into three groups, i.e., steroid glycosides, triterpene glycosides, and flavonoid and phenolic glycosides. Typical synthetic approaches are discussed, showing the demanding tactics for regio‐ and stereo‐controlled installation of glycans and overall manipulation of protecting groups. These expedient and scalable synthetic approaches have provided practical alternatives to the accessibility of these TCM components and thus opportunities for their in depth biological and pharmacological studies.

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“…Baicalein was treated with Ac 2 O and AcONa to obtain fully acetylated compound 14, which was sequentially benzylated with BnBr and hydrogenolysed with Pd(OH) 2 /C to provide acceptor 4 in 90% yield for the two steps. 11 The synthesis of the acceptor 6 was started with scutellarein, which was treated with dichlorodiphenylmethane in diphenyl ether to produce the desired compound 15 in 83% yield. 19 Subsequently, the C 4' -OH of compound 15 was selectively reacted with MeI to afford 16, 20 and then the benzophenone ketal group was removed under the hydrolysis conditions with 80% AcOH in H 2 O to obtain 17 in 95% yield.…”

Section: Resultsmentioning

confidence: 99%

“…Chemical synthesis could provide a feasible way to solve the problem, and many groups have made great efforts to provide sufficient amounts of flavonoid glycosides through chemical synthesis. [10][11][12] Recently, Wu et al 13 reported two novel flavonoid glycosides, oroxin C (baicalein 7-O-β-d-glucopyranosyl-(1→6)-βd-glucopyranosyl-(1→6)-β-d-glucopyranoside, 1) and oroxin D (scutellarein 4'-methyl ether 7-O-β-d-glucopyranosyl-(1→6) -β-d-glucopyranoside, 2), isolated from the seeds of Oroxylum indicum as a part of a program to search for potent and effective antidiabetic agents. However, the formidable task of isolating these two natural products turned out to be an obstacle for further pharmacological research, and so it is useful for syntheses of the two novel flavonoid glycosides 1 and 2 to be completed to enable further SAR investigation.…”

Section: Introductionmentioning

confidence: 99%

Concise synthesis and antidiabetic activity of natural flavonoid glycosides, oroxins C and D, isolated from the seeds of Oroxylum indium

Wang

Tong

et al. 2020

Journal of Chemical Research

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The first concise synthesis of natural flavonoid glycosides, oroxins C (1) and D (2), which were isolated from the seeds of Oroxylum indicum, was efficiently achieved by a convergent strategy. The synthesized natural products 1 and 2 were evaluated for their inhibitory activities against α-glucosidase, α-amylase, and lipase. Compound 1 showed strong α-amylase and lipase inhibition, with IC50 values of 210 and 190 μM, respectively, but exhibited no inhibitory activity against α-glucosidase. Compound 2 showed strong inhibition against α-glucosidase and lipase, with the respective IC50 values of 180 and 80 μM.

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Efficient synthesis of baicalin and its analogs

Cited by 16 publications

References 35 publications

First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B

First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4‐O‐Glycosides Phyllanthusmin D and 4′′‐O‐Acetylmananthoside B

Synthesis of the Diverse Glycosides in Traditional Chinese Medicine

Concise synthesis and antidiabetic activity of natural flavonoid glycosides, oroxins C and D, isolated from the seeds of Oroxylum indium

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