An asymmetric synthesis of isopodophyllotoxin

Pelter, Andrew; Ward, Robert S.; Li, Qianrong; Píš, Jaroslav

doi:10.1016/s0957-4166(00)86243-6

Cited by 31 publications

(5 citation statements)

References 6 publications

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“…amorphous powder; [α] 25 D 0 ( c 0.5, CHCl 3 ). The 1 H and 13 C NMR spectra were identical with literature data. ,, …”

Section: Methodssupporting

confidence: 59%

“…The five known aryltetralin lignans deoxypicropodophyllotoxin ( 3 ), 22 (±)-β-apopicropodophyllin ( 4 ), 20 , 23 , 24 (−)-desoxypodophyllotoxin ( 5 ), 25 (−)-yatein ( 6 ), 26 and β-peltatin-5- O -β- d -glucopyranoside ( 7 ) 27 were also isolated. Their structures were determined by comparison of their 1 H NMR spectroscopic, mass spectrometric, and optical rotation values with the data reported in the literature, except for the case of β-apopicropodophyllin ( 4 ), which was optically inactive.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H and 13 C NMR spectra were identical with literature data. 20,23,24 Acid Hydrolysis of Compounds 1 and 2. Compound 1 (2 mg) was dissolved in dilute citrate−phosphate buffer (pH 7.0, 4 mL), and β-D-glucosidase (4 mg) was added.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Liu¹,

Young²,

Rakotondraibe³

et al. 2015

J. Nat. Prod.

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The two new lignans 3α-O-(β-d-glucopyranosyl)desoxypodophyllotoxin (1) and 4-O-(β-d-glucopyranosyl)dehydropodophyllotoxin (2) were isolated from Cleistanthus boivinianus, together with the known lignans deoxypicropodophyllotoxin (3), (±)-β-apopicropodophyllin (4), (−)-desoxypodophyllotoxin (5), (−)-yatein (6), and β-peltatin-5-O-β-d-glucopyranoside (7). The structures of all compounds were characterized by spectroscopic techniques. Compounds 1, 4, and 5 showed potent antiproliferative activities against the A2780 ovarian cancer cell line, with IC50 values of 33.0 ± 3.6, 63.1 ± 6.7, and 230 ± 1 nM, respectively. Compounds 2 and 7 showed only modest A2780 activities, with IC50 values of 2.1 ± 0.3 and 4.9 ± 0.1 μM, respectively, while compounds 3 and 6 had IC50 values of >10 μM. Compound 1 also had potent antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 value of 20.5 nM, and compound 4 exhibited modest antiproliferative activity against the A2058 human caucasian metastatic melanoma and MES-SA human uterine sarcoma cell lines, with IC50 values of 4.6 and 4.0 μM, respectively.

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“…amorphous powder; [α] 25 D 0 ( c 0.5, CHCl 3 ). The 1 H and 13 C NMR spectra were identical with literature data. ,, …”

Section: Methodssupporting

confidence: 59%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Liu¹,

Young²,

Rakotondraibe³

et al. 2015

J. Nat. Prod.

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show abstract

“…However, the regioselectivity observed is frequently only modest when non-symmetrical dienophiles are used. [55][56][57][58][59][60] For this reason a number of approaches have used simple symmetrical maleate systems exploiting the greater accessibility of the C3 carbonyl group for subsequent selective epimerisation and reduction of the cycloadduct. [61,62] The particular problems of fumarate cycloadditions are illustrated by the early work of Durst (Scheme 16).…”

Section: C-ring Formation By Cycloaddition Reactionsmentioning

confidence: 99%

Advances in the Synthesis of Aryltetralin Lignan Lactones

Sellars

Steel

2007

Eur J Org Chem

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Etoposide and tenoposide, derivatives of the aryltetralin lignan lactone podophyllotoxin (5), are clinically important anticancer agents. The structure of podophyllotoxin includes four contiguous chiral centres contained within a stereochemically unstable trans‐fused tetrahydronaphthalene lactone skeleton. Reflecting this challenging structure and important biological role there has been long‐standing interest in developing efficient stereocontrolled syntheses of this class of natural product. This microreview summarises the key developments towards this end focussing on more recent developments both from within the authors group and elsewhere.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…There is widespread interest in the synthesis and properties of these natural or semisynthetic compounds,12, 16, 22–26 and it is useful therefore to explore every avenue to aid in the structural elucidation and characterization of such compounds. A mass spectrometer equipped with an electrospray ionization source and an ion trap analyzer linked to a time‐of‐flight mass analyzer (ESI‐IT‐TOF) is effective for the structural analysis of such natural products.…”

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confidence: 99%

A fragmentation study of two compounds related to 4′‐demethylepipodophyllotoxin in negative ion electrospray ionization by MSⁿ ion‐trap time‐of‐flight mass spectrometry

Yan

2008

Rapid Comm Mass Spectrometry

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High-resolution electrospray ionization multistage tandem mass spectrometry (MS 1-7) in negative ion mode was used to determine the accurate masses and fragmentation pathways of two compounds, 4'-demethylepipodophyllotoxin and 4'-demethyl-4-azido-4-deoxyepipodophyllotoxin, which are key intermediate compounds for the preparation of podophyllotoxin-type anti-cancer drugs. The deprotonated molecules [M-H]* of both compounds were readily observed in the conventional single-stage mass spectra due to the presence of the phenolic hydroxyl group in the molecules. Abundant information on the product ions was obtained from tandem mass spectra (MS 2-7) in negative ion mode. Based on the exact masses acquired from 14 different tandem mass spectra, a similar MSn fragmentation pathway was proposed for both compounds. A characteristic product ion produced in the MS 2-4 product ion scan experiments is the cyclohexylenetrione anion [M-H-2Me-RH]* or [M-H-RH-2Me]* at m/z 351 (C19H11O7) formed by the consecutive losses of two CH3 radicals at the 3'- and 5'-positions and the neutral loss of RH, where R = a 4-substituted group (-OH or -N3), from the [M-H]* ion. This anion may be considered as diagnostic for the presence of this type of compound. The other common cleavages are the neutral losses of CO at least two times in the MS 6,7 product ion spectra. The results of this work could serve as an effective tool for the detection or determination of other derivatives of 4'-demethyl-4beta-substituted podophyllotoxin, which are widely used as intermediates for the preparation of anti-tumor drugs.

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An asymmetric synthesis of isopodophyllotoxin

Cited by 31 publications

References 6 publications

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Advances in the Synthesis of Aryltetralin Lignan Lactones

A fragmentation study of two compounds related to 4′‐demethylepipodophyllotoxin in negative ion electrospray ionization by MSⁿ ion‐trap time‐of‐flight mass spectrometry

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An asymmetric synthesis of isopodophyllotoxin

Cited by 31 publications

References 6 publications

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Antiproliferative Compounds from Cleistanthus boivinianus from the Madagascar Dry Forest1

Advances in the Synthesis of Aryltetralin Lignan Lactones

A fragmentation study of two compounds related to 4′‐demethylepipodophyllotoxin in negative ion electrospray ionization by MSn ion‐trap time‐of‐flight mass spectrometry

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A fragmentation study of two compounds related to 4′‐demethylepipodophyllotoxin in negative ion electrospray ionization by MSⁿ ion‐trap time‐of‐flight mass spectrometry