Formal synthesis of piperazinomycin, a novel antifungal antibiotic

Ghosh, Samir; Kumar, Ankesh; Mehta, G. N.; Soundararajan, R.; Sen, Subhabrata

doi:10.3998/ark.5550190.0010.707

Cited by 20 publications

(14 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As shown in Scheme 7, compound 23 was prepared from 22 via an intramolecular O-arylation of a phenol with an arylboronic acid, and was subsequently transformed into the natural product 24 using a previously reported reduction with borane, followed by O-demethylation. 22 Many other relevant compounds have been obtained by complete reduction of both carbonyl groups in suitable diketopiperazine precursors. Among them, we will mention as illustrative examples the chiral tertiary amines 25, developed as asymmetric catalysts for the Baylis-Hillman reaction, 23 and also polycyclic compounds 26, which were prepared in the course of a pharmacophore search for allosteric ligands of the muscarinic M 2 receptor 24 (Scheme 8).…”

Section: Synthetic Methods Involving the Reduction Of Dkp Carbonyl Gr...mentioning

confidence: 99%

Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

et al. 2012

View full text Add to dashboard Cite

show abstract

Section: Synthetic Methods Involving the Reduction Of Dkp Carbonyl Gr...mentioning

confidence: 99%

Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

et al. 2012

View full text Add to dashboard Cite

show abstract

“…228 Scheme 9 Copper-mediated macrocyclization reactions used in the preparation of 73. 160,238 Another copper-induced macrocyclization applied for the formation of the aryl-aryl ether bond was described by Sen in 2009 (Scheme 9, right). 238 Here, the Chan-Lam-Evans procedure was used, [239][240][241] producing the cyclic intermediate 87 from the boronic acid 86.…”

Section: Isodityrosine-containing Peptidesmentioning

confidence: 99%

“…160,238 Another copper-induced macrocyclization applied for the formation of the aryl-aryl ether bond was described by Sen in 2009 (Scheme 9, right). 238 Here, the Chan-Lam-Evans procedure was used, [239][240][241] producing the cyclic intermediate 87 from the boronic acid 86. This reaction proceeded at room temperature, but gave the constrained diketopiperazine 87 only in 33% yield.…”

Section: Isodityrosine-containing Peptidesmentioning

confidence: 99%

Strained cyclophane natural products: Macrocyclization at its limits

2012

View full text Add to dashboard Cite

Cyclophane natural products comprise an intriguing class of structurally diverse compounds. As inherent for all cyclic compounds regardless of their origin, macrocyclization is naturally the most decisive step, which defines the overall efficiency of the synthetic pathway. Especially in small cyclophane molecules, this key step constitutes an even greater challenge. Due to the strain imparted by the macrocyclic system, free rotation of the benzene ring(s) is often restricted depending on both the constitution of the tether and the aromatic portions. Not surprisingly, the synthesis of natural cyclophanes with their often outstanding pharmaceutical activities and the inherent issues associated with their preparation has attracted much attention among the synthetic community. In particular, it stimulated the development of new strategies for the ring-closing step, as often otherwise well established and robust reactions fail to perform effectively. In this review, we describe the challenges synthetic chemists are facing during the synthesis of this small, but structurally and biologically fascinating class of natural products, concentrating on the representatives exhibiting configurational stability. The main focus will be on the different concepts for the installation of the macrocyclic system, in most cases the central problem in assembling these extremely rigid molecules.

show abstract

“…An efficient approach to the green synthesis of glycoluryls in an aqueous medium using P 4 O 10 as a catalyst, under mild conditions with the possibility of recycling both solvent and catalyst, is reported in Ref. [39] More recently, in a number of works [40][41][42] it was found that etidronic acid (HEDP) proved to be a convenient "green" catalyst in 3-component reactions of the formation of dihydropyrimidones using carbonyl compounds with an active methylene group, urea and aldehydes as under traditional conditions, [40,41] and under microwave synthesis. [42] However, examples of the use of HEDP as a catalyst in the reactions of 1, 2-dicarbonyl compounds with ureas are still not known.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

Бакибаев

Uhov

Malkov

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as "Green catalyst." So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80 C-90 C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.

show abstract

Formal synthesis of piperazinomycin, a novel antifungal antibiotic

Abstract: An alternative synthesis of piperazinomycin is disclosed. The approach is based on an intramolecular O-arylation of arylboronic acid with phenol for formation of the macrocyclic biaryl ether.

Cited by 20 publications

References 6 publications

Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

Privileged scaffolds in synthesis: 2,5-piperazinediones as templates for the preparation of structurally diverse heterocycles

Strained cyclophane natural products: Macrocyclization at its limits

Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2‐dicarbonyl compounds using etidronic acid as a “green catalyst”

Contact Info

Product

Resources

About