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Zur Synthese von (−)-und (+)-Griseofulvin und ihrer Diastereomeren.

Totalsynthese von Griseofulvin.

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: Synthese versuche in der Griseofulvinreihe.

All the synthesised compounds were characterized and identified by using different physico-chemical parameters. Such as, TLC, melting point, elemental analysis, IR and1HNMR. From the literature survey it reveals that, the substituted imidazoles have been reported for number of pharmacological activities. The prepared compounds were screened for their anti-bacterial activity by using cup-plate agar diffusion method against various gram positive, gram negative and fungal stains. Some of the compounds show comparable activity with that of the standard (Ciprofloxacin and Griseofulvin).

Eine Totalsynthese von Griseofulvin.

N2 - We report two types of modifications to the natural product griseofulvin as strategies to improve solubility and metabolic stability: the conversion of aryl methyl ethers into aryl difluoromethyl ethers at metabolic hotspots and the conversion of the C-ring ketone into polar oximes. The syntheses of the analogues are described together with their solubility, metabolic half-life in vitro and antiproliferative effect in two cancer cell lines. We conclude that on balance, the formation of polar oximes is the most promising strategy for improving the properties of the analogues.

Synthesis of Compounds related to Griseofulvin.

: The Total Synthesis of Griseofulvin.

AB - The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.

N2 - The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.

The Total Synthesis of Griseofulvin.

: Production of the 2′-Ethoxy Analogue of Griseofulvin by Biosynthesis.

We report two types of modifications to the natural product griseofulvin as strategies to improve solubility and metabolic stability: the conversion of aryl methyl ethers into aryl difluoromethyl ethers at metabolic hotspots and the conversion of the C-ring ketone into polar oximes. The syntheses of the analogues are described together with their solubility, metabolic half-life in vitro and antiproliferative effect in two cancer cell lines. We conclude that on balance, the formation of polar oximes is the most promising strategy for improving the properties of the analogues.

AB - We report two types of modifications to the natural product griseofulvin as strategies to improve solubility and metabolic stability: the conversion of aryl methyl ethers into aryl difluoromethyl ethers at metabolic hotspots and the conversion of the C-ring ketone into polar oximes. The syntheses of the analogues are described together with their solubility, metabolic half-life in vitro and antiproliferative effect in two cancer cell lines. We conclude that on balance, the formation of polar oximes is the most promising strategy for improving the properties of the analogues.

: A Total Synthesis of Racemic Griseofulvin.
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  • : Biosynthesis of Griseofulvin.

    T1 - An improved synthetic method for dl-griseofulvin and its 2'-s-analogue

  • : A Stereospecific Total Synthesis of Griseofulvin.

    : Biosynthesis of Griseofulvin: the Methylated Benzophenone Intermediates.

  • Application to the Total Synthesis of Griseofulvin.

    : A Total Synthesis of Griseofulvin and its Optical Antipode.

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: Synthesis in the Griseofulvin Series: 6′-Demethylgriseofulvin.

The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.

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