Four-Component Condensations and Related Reactions

Gokel, George W.; Lüdke, G.; Ugi, I.

doi:10.1016/b978-0-12-706150-4.50013-7

Cited by 51 publications

(17 citation statements)

References 52 publications

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“…Rearrangement via acyl group migration onto the nitrogen atom derived from the imine generates the final product ( Fig. 1A) (8)(9)(10)(11). The Ugi reaction is well suited for diversityoriented synthesis applicable in drug discovery (12)(13)(14)(15).…”

Section: Discussionmentioning

confidence: 99%

Asymmetric phosphoric acid–catalyzed four-component Ugi reaction

Zhang

et al. 2018

Science

173

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The Ugi reaction constructs α-acylaminoamide compounds by combining an aldehyde or ketone, an amine, a carboxylic acid, and an isocyanide in a single flask. Its appealing features include inherent atom and step economy together with the potential to generate products of broad structural diversity. However, control of the stereochemistry in this reaction has proven to be a formidable challenge. We describe an efficient enantioselective four-component Ugi reaction catalyzed by a chiral phosphoric acid derivative that delivers more than 80 α-acylaminoamides in good to excellent enantiomeric excess. Experimental and computational studies establish the reaction mechanism and origins of stereoselectivity.

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Section: Discussionmentioning

confidence: 99%

Asymmetric phosphoric acid–catalyzed four-component Ugi reaction

Zhang

et al. 2018

Science

173

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“…70 After switching from the TBDPS ether to the acetate, simultaneous cleavage of the Boc group and the MOM ether gave the aminophenol, which was readily cyclized to afford 75 . The dioxopiperazine 75 was converted to the cyclization precursor 76 by a four-step sequence involving mesylation, introduction of a Boc group onto the lactam nitrogen, partial reduction of the ring carbonyl group, and dehydration.…”

Section: Synthetic Studies Of Et-743mentioning

confidence: 99%

Ecteinascidins. A review of the chemistry, biology and clinical utility of potent tetrahydroisoquinoline antitumor antibiotics

et al. 2015

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The Ecteinascidin family comprises a number of biologically active compounds, containing two to three tetrahydroisoquinoline subunits. Although isolated from marine tunicates, these compounds share a common pentacyclic core with several antimicrobial compounds found in terrestrial bacteria. Among the tetrahydroisoquinoline natural products, Ecteinascidin 743 (Et-743) stands out as the most potent antitumor antibiotics that it is recently approved for treatment of a number of soft tissue sarcomas. In this article, we will review the backgrounds, the mechanism of action, the biosynthesis, and the synthetic studies of Et-743. Also, the development of Et-743 as an antitumor drug is discussed.

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“…In this case the intermediate 22, generated by interaction with the aldehyde and the isocyanide, cannot be transformed into the corresponding trans-fused β-lactam because of steric bias, and an alternative mechanism operates, accounting for the formation of compound 23. A 5-centre-4-component Ugi reaction (U-5C-4CR), [29] which is typical when α-amino acids are employed, takes place with the formation of the methyl ester 23 through displacement of 22 by the methanol used as the solvent. The results were promising in that, at least in few cases, very high diastereoselectivities were observed.…”

Section: Norbornane/ene Amino Acids As Bifunctional Building Blocks Imentioning

confidence: 99%

A Marriage of Convenience: Combining the Power of Isocyanide‐Based Multicomponent Reactions with the Versatility of (Hetero)norbornene Chemistry

2010

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Isocyanide‐based multicomponent reactions (I‐MCRs) represent a milestone in combinatorial chemistry. Recently, efforts have been made to include I‐MCRs in tandem or sequential pathways to synthesise more complex molecules, and the bicyclo[2.2.1]heptene (norbornene) moiety has been demonstrated to be a very versatile scaffold when employed to broaden the scope of the multicomponent approach, making it perfectly suited for diversity‐oriented synthesis. In addition to this, the (hetero)norbornane/norbornene scaffold has been shown to influence the stereocontrol of the multicomponent condensation strongly, in some instances making this synthetic approach completely stereoselective. Finally, because of their intrinsic complexity, the resulting molecular entities can find many applications, from biology to polymer science. This review summarises the results obtained in this emerging field.

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Four-Component Condensations and Related Reactions

Cited by 51 publications

References 52 publications

Asymmetric phosphoric acid–catalyzed four-component Ugi reaction

Asymmetric phosphoric acid–catalyzed four-component Ugi reaction

Ecteinascidins. A review of the chemistry, biology and clinical utility of potent tetrahydroisoquinoline antitumor antibiotics

A Marriage of Convenience: Combining the Power of Isocyanide‐Based Multicomponent Reactions with the Versatility of (Hetero)norbornene Chemistry

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