First example of an Ugi type reaction on phenylsulfinimine-avermectin B1 derivatives

Callens, Emmanuel; Hüter, Ottmar; Lamy, Emmanuel; Lüthi, Patrick; Winkler, Tammo; Jung, Pierre M. J.

doi:10.1016/j.tetlet.2006.11.089

Cited by 7 publications

(3 citation statements)

References 13 publications

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“…Another agrochemical application of MCR is the short synthesis of novel avermectin derivatives as insecticital agents through the diastereoselective Ugi reaction to an phenylsulfinimide intermediate. 251 Fipronil is a new fluorinated pyrazole with high insecticide activity and derivatives thereof have been synthesized by the Mannich reaction of hydrazones coupled with a [4 + 1] cycloaddition with isocyanides. 252 Key diketopiperazine moieties in the DNA targeting anticancer natural products naphthyridinomycin, lemonomycin and the clinical liposarcoma compound ecteinascidin have been assembled using Ugi-MCRs as key steps (Scheme 55).…”

Section: Miscellaneousmentioning

confidence: 99%

“…Thus, the effective concentration to kill 80% of the pathogen Phytophthora infestans (grape downy mildew) is only 100 μg/l (EC 80 ). Another agrochemical application of MCR is the short synthesis of novel avermectin derivatives as insecticital agents through the diastereoselective Ugi reaction to an phenylsulfinimide intermediate . Fipronil is a new fluorinated pyrazole with high insecticide activity and derivatives thereof have been synthesized by the Mannich reaction of hydrazones coupled with a [4 + 1] cycloaddition with isocyanides …”

Section: Mcrs By Target Classmentioning

confidence: 99%

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Chemistry and Biology Of Multicomponent Reactions

2012

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Section: Miscellaneousmentioning

confidence: 99%

Section: Mcrs By Target Classmentioning

confidence: 99%

Chemistry and Biology Of Multicomponent Reactions

2012

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“…Various efforts have been made to obtain compounds with higher potency and broader activity spectra by modifying the avermectin B1a molecule. 13,[17][18][19] For example, ivermectin (22,23-dihydro-avermectin B1a, Fig. 1), has the same excellent potency and spectrum against nematode parasites as avermectin B1a, albeit with a greater safety prole.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and insecticidal activities of 5-deoxyavermectin B2a oxime ester derivatives

et al. 2018

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A Half‐Century of the Ugi Reaction: Classic Variant

Ullrich

Kazmaier

2023

Organic Reactions

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The classic Ugi reaction is a four‐component coupling process that involves a carboxylic acid, a carbonyl compound, an amine, and an isocyanide. All reaction components are in a dynamic equilibrium with several intermediates, until an irreversible intramolecular 1,4‐ O → N acyl transfer leads to the formation of an N ‐acylamino acid amide. If chiral components are used in this reaction, a mixture of diastereomers is generally formed with moderate‐to‐low stereoselectivity. The broad scope of substrates that can be used in the Ugi reaction allows for the straightforward synthesis of libraries of structurally related amino acid and peptide derivatives. Therefore, this methodology is often applied to the synthesis of drugs, drug‐like molecules, and natural products. This chapter describes different variations of classic Ugi reactions, including the use of functionalized and cleavable reaction components to illustrate the broad scope of the reaction. In addition, applications in target‐directed synthesis and comparisons to other related multicomponent reactions are presented. Tabular surveys are organized according to the isocyanides used. The literature is discussed from the first disclosure of an Ugi reaction in 1961 through to the end of 2012.

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First example of an Ugi type reaction on phenylsulfinimine-avermectin B1 derivatives

Cited by 7 publications

References 13 publications

Chemistry and Biology Of Multicomponent Reactions

Chemistry and Biology Of Multicomponent Reactions

Synthesis and insecticidal activities of 5-deoxyavermectin B2a oxime ester derivatives

A Half‐Century of the Ugi Reaction: Classic Variant

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