Synthesis of farinomalein

Miles, William H.; Yan, Ming

doi:10.1016/j.tetlet.2010.01.083

Cited by 15 publications

(10 citation statements)

References 28 publications

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“…Recently, a three-step synthesis of Farinomalein has been reported by Miles and Yan. [3] The sequence is based on the reaction of isovaleraldehyde and glyoxylic acid to give a γhydroxybutenolide. Successive oxidation to the corresponding anhydride and treatment with βalanine affords Farinomalein.…”

Section: Introductionmentioning

confidence: 99%

“…Successive oxidation to the corresponding anhydride and treatment with βalanine affords Farinomalein. However, the Authors themselves state that their synthesis is difficult to scale-up [3] , due to the use of hazardous and expensive oxidant Dess-Martin periodinane. Herein we report a different synthetic approach to Farinomalein, developed in four steps with high yield and without using any hazardous chemical.…”

Section: Introductionmentioning

confidence: 99%

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Improved Synthesis of Farinomalein and Its Analogs

Aiwale

Sardi

Dallavalle

2013

Synthetic Communications

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Improved Synthesis of Farinomalein and Its Analogs

Aiwale

Sardi

Dallavalle

2013

Synthetic Communications

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“…It showed potent activity against the plant pathogen Phytophthora sojae [ 68 ]. It can be synthesized in two steps from a readily available γ-hydroxybutenolide [ 69 ]. The activities against Phytophthora sojae and Aphanomyces cochlioides were confirmed [ 70 ].…”

Section: Secondary Metabolites (Sms) From Isaria Farinosamentioning

confidence: 99%

Secondary Metabolites and the Risks of Isaria fumosorosea and Isaria farinosa

et al. 2019

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Isaria fumosorosea and Isaria farinosa are important entomopathogenic fungi with a worldwide distribution and multiple host insects. However, the concerns about the safety risks of myco-pesticides have been attracting the attention of researchers and consumers. Secondary metabolites (SMs), especially the mycotoxins, closely affect the biosafety of Isaria myco-insecticides. In the last forty years, more than seventy SMs were identified and isolated from I. fumosorosea and I. farinose. The SMs of I. fumosorosea include the mycotoxins of non-ribosomal peptides (NRPs) (beauvericin and beauverolides), terpenes (trichocaranes and fumosorinone), lactone compounds (cepharosporolides), acids (dipicolinic acid and oxalic acid), etc. Meanwhile, the NRP mycotoxins (cycloaspeptides) and the terpene compounds (farinosones and militarinones) are the main SMs in I. farinosa. Although several researches reported the two Isaria have promised biosafety, the bioactivities and the safety risks of their SMs have not been studied in detail so far. However, based on existing knowledge, most SMs (i.e., mycotoxins) do not come from Isaria myco-insecticide itself, but are from the host insects infected by Isaria fungi, because only the hosts can provide the conditions for fungal proliferation. Furthermore, the SMs from Isaria fungi have a very limited possibility of entering into environments because many SMs are decomposed in insect cadavers. The biosafety of Isaria myco-insecticides and their SMs/mycotoxins are being monitored. Of course, SMs safety risks of Isaria myco-insecticides need further research.

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“…The first synthetic approach to farinomalein A was reported by Miles and Yan. 3 The sequence is based on the reaction of isovaleraldehyde and glyoxylic acid to give a γ-hydroxybutenolide.…”

mentioning

confidence: 99%

“…Successive oxidation to the corresponding anhydride and treatment with β-alanine affords farinomalein A. However, the Authors themselves state that their synthesis is difficult to scaleup, 3 due to the use of the hazardous and expensive oxidant Dess-Martin periodinane. More recently, an alternative strategy for the preparation of farinomalein A has been reported by us.…”

mentioning

confidence: 99%

Synthesis of natural maleimides farinomaleins C–E and evaluation of their antifungal activity

Lahore

Aiwale

Sardi

et al. 2014

Tetrahedron Letters

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A practical and convenient synthesis of naturally occurring farinomaleins C-E was achieved starting from readily available ethyl 3-methyl-2-oxobutyrate and triethyl phosphonoacetate. The key steps of the sequence included a Horner-Wadsworth-Emmons condensation to obtain the precursor farinomalein A and coupling with suitable alcohols to install the chain. The synthesis of farinomalein D has been achieved starting from (R)-isopropylideneglycerol on the basis of which the S configuration was assigned to the natural compound. The antifungal activity of the synthesized compounds was evaluated against Cladosporium cladosporioides. .

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Synthesis of farinomalein

Cited by 15 publications

References 28 publications

Improved Synthesis of Farinomalein and Its Analogs

Improved Synthesis of Farinomalein and Its Analogs

Secondary Metabolites and the Risks of Isaria fumosorosea and Isaria farinosa

Synthesis of natural maleimides farinomaleins C–E and evaluation of their antifungal activity

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