Condensation of succinic anhydride with N-benzylidene-N-methylamine. Stereoselective synthesis of trans- and cis-1-methyl-4-carboxy-5-phenyl-2-pyrrolidinone

Castagnoli, Neal

doi:10.1021/jo01262a081

Cited by 107 publications

(93 citation statements)

References 4 publications

(7 reference statements)

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“…2. According to the occurrence the top scaffold is the Ugi-β-lactam followed by Ugi-tetrazole-3CR scaffold, Ugi-hydantoin, U-4CR, 18 Castagnolli-3CR, 19,20 Doebner-3CR 21 and van Leusen 22 are highest scoring amongst the 27 MCR scaffold space populated with >30 million individual compounds. Several potent MDM2 binders based on these scaffolds and cocrystallized with the MDM2 receptor have been described by us and others in the past.…”

Section: Resultsmentioning

confidence: 99%

Scaffold hopping via ANCHOR.QUERY: β-lactams as potent p53-MDM2 antagonists

et al. 2017

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Section: Resultsmentioning

confidence: 99%

Scaffold hopping via ANCHOR.QUERY: β-lactams as potent p53-MDM2 antagonists

et al. 2017

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“…The cycloaddition of imines with succinic anhydride in a one-pot approach to construct the γ-lactam moiety in high yield was first reported three decades ago by Castagnoli et al [34](Scheme 16, Equation 1). A mechanistic study was not published until 1983 when Cushman studied the electronic and steric effects on the stereochemical outcome [35].…”

Section: New One-pot Reactions Used In the Asymmetric Constructionmentioning

confidence: 99%

New One-Pot Methodologies for the Modification or Synthesis of Alkaloid Scaffolds

Wahba

Hamann

2010

Marine Drugs

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There are several avenues by which promising bioactive natural products can be produced in sufficient quantities to enable lead optimization and medicinal chemistry studies. The total synthesis of natural products is an important, but sometimes difficult, approach and requires the development of innovative synthetic methodologies to simplify the synthesis of complex molecules. Various classes of natural product alkaloids are both common and widely distributed in plants, bacteria, fungi, insects and marine organisms. This mini-review will discuss the scope, mechanistic insights and enantioselectivity aspects of selected examples of recently developed one-pot methods that have been published in 2009 for the synthesis of substituted piperidines, quinolizidines, pyrrolidines, hexahydropyrrolizines, octahydroindolizines and γ-lactams. In addition, progress on the synthesis of β-carboline (manzamine) alkaloids will also be discussed.

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“…[20] For a long time (since its discovery in 1969 [21] ) this reaction was thought to be applicable to five-and sixmembered cyclic anhydrides [homophthalic anhydride, or HPA (2), being one of the most reactive ones [22] ], and thus it could only give access to δand γ-lactams (such as 3, usually ob- Figure 1. [20] For a long time (since its discovery in 1969 [21] ) this reaction was thought to be applicable to five-and sixmembered cyclic anhydrides [homophthalic anhydride, or HPA (2), being one of the most reactive ones [22] ], and thus it could only give access to δand γ-lactams (such as 3, usually ob- Figure 1.…”

Section: Introductionmentioning

confidence: 99%