Total synthesis of (±) epipodophyllotoxin via a (3 + 2)-cycloaddition strategy

Vyas, Dolatrai M.; Skonezny, Paul M.; Jenks, T. A.; Doyle, Terrence W.

doi:10.1016/s0040-4039(00)84725-5

Cited by 39 publications

(9 citation statements)

References 14 publications

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“…(2) with benzaldehydes (3a,b) separately in the presence of sodium hydroxide in ethanol-water mixture [5,6]. The cyclopropyl ketones (5a,b) were prepared in high yields by the reaction of chalcones (4a,b) with trimethyl sulphoxonium iodide in presence of sodium hydride in dry benzene [7][8][9]. The tetralones (6 and 7) were prepared in good yields by the intramolecular cyclization of cyclopropyl ketones (5a,b) in presence of anhydrous stannic chloride and acetic anhydride in dry dichloromethane [10,11].…”

Section: General Procedures For the Synthesis Of Tetralones (6 7)mentioning

confidence: 99%

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

2016

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Podophyllotoxin has captured the attention of chemists all over the world for its biological activity. It was isolated from many plants of Podophyllum species such as Podophyllum emodi, Podophyllum peltatum and others. It mainly exhibits anticancer, antimitotic, antimalarial, anti-aids and other activities. Its use is restricted due to its toxicity and unfavourable solubility. It was aimed to synthesize some new heterocyclic analogues of podophyllotoxin by changing the substituents by changing lactone ring with pyrazoline ring and substituents in ring C with hydrogen and methoxy group. Chalcones were prepared by Claisen-Schmidt reaction of 1,3-methylene dioxyacetophenone with benzaldehyde and p-anisaldehyde. The reaction of chalcone with trimethylsulphoxonium iodide in presence of sodium hydride gave cyclopropyl ketone. Intramolecular cyclization reaction of cyclopropyl ketone gave tetralone intermediates of podophyllotoxin. They are obtained in good yields. The structure of all the products was confirmed by spectral data.

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Section: General Procedures For the Synthesis Of Tetralones (6 7)mentioning

confidence: 99%

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

2016

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“…The tetralone esters (9a-d) were prepared in good yields by intramolecular cyclization of cyclopropyl keto esters (8a-d) in the presence of anhydrous stannic chloride and acetic anhydride in dry dichloromethane [20,21]. The structures of tetralone esters were based on IR, 1 H NMR, Mass spectra and elemental analysis data.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and study of antimicrobial activity of new tetralone esters

et al. 2014

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“…This challenging transformation can be addressed by carrying out the isomerisation at an earlier stage of the synthesis prior to introduction of the C3 substituent or following hydrolysis to the keto-acid. [86,87] Importantly, the former approach facilitates the stereocontrolled introduction of the C3 hydroxymethyl group as seen in the work of Vyas and Wong (Scheme 26). Scheme 26. These approaches have largely established the C1 stereochemistry early in the synthesis and used this to control the introduction of the remaining stereocentres.…”

Section: Functionalisation Of the Preformed C Ringmentioning

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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Total synthesis of (±) epipodophyllotoxin via a (3 + 2)-cycloaddition strategy

Cited by 39 publications

References 14 publications

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

Synthesis and study of antimicrobial activity of new tetralone esters

Advances in the Synthesis of Aryltetralin Lignan Lactones

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