Total Synthesis of (−)-Cylindricine H

Piccichè, Miriam; Pinto, Alexandre; Griera, Rosa; Bosch, Joan; Amat, Mercedes

doi:10.1021/acs.orglett.2c02004

Cited by 12 publications

(4 citation statements)

References 34 publications

(14 reference statements)

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“…Meyers’ lactamization reaction has been widely used for the stereoselective synthesis of bicyclic lactams, which may be utilized as chiral building blocks for the stereoselective construction of five- and six-membered nitrogen-containing heterocycles [ 27 , 28 ]. It is a well-known tool for the synthesis of natural products (especially alkaloids) from phenylglycinol-derived bi- and tricyclic lactams [ 29 , 30 , 31 ]. However, to the best of our knowledge, this methodology has not been extended to derive 4-piperidone δ–keto-ester until the work of our group [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

et al. 2023

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The concept of privileged structure has been used as a fruitful approach for the discovery of novel biologically active molecules. A privileged structure is defined as a semi-rigid scaffold able to display substituents in multiple spatial directions and capable of providing potent and selective ligands for different biological targets through the modification of those substituents. On average, these backbones tend to exhibit improved drug-like properties and therefore represent attractive starting points for hit-to-lead optimization programs. This article promotes the rapid, reliable, and efficient synthesis of novel, highly 3-dimensional, and easily functionalized bio-inspired tricyclic spirolactams, as well as an analysis of their drug-like properties.

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Section: Resultsmentioning

confidence: 99%

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

et al. 2023

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“…590 The rst total syntheses of (−)-cylindricine H 1468 (ref. 591) and iheyamine B 1469 (ref. 592) have been reported, leading to assignment of their respective absolute congurations.…”

Section: Reviewmentioning

confidence: 99%

Marine natural products

Carroll,

Copp,

Grkovic

et al. 2024

Nat. Prod. Rep.

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“…The data that support the findings of this study are available in the Supporting Information of this article. The authors have cited additional references within the Supporting Information [6b–g,8a,12b,15a,17–21] …”

Section: Data Availability Statementmentioning

confidence: 99%

A Cytochrome P450 Catalyzes Oxidative Coupling Formation of Insecticidal Dimeric Indole Piperazine Alkaloids

He,

Zhang,

Zou

2024

Angewandte Chemie

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Cytochrome P450 (CYP450)‐catalysed oxidative coupling is an efficient strategy of using simple building blocks to construct complex structural scaffolds of natural products. Among them, heterodimeric coupling between two different monomers is relatively scarce and the corresponding CYP450s are largely undiscovered. Herein, we discovered a fungal CYP450 (CpsD) and its associated cps cluster from 37208 CYP450s of Pfam PF00067 family member database and subsequently identified a group of new skeleton indole piperazine alkaloids (campesines A‐G) by combination of genome mining and heterologous synthesis. Importantly, CYP450 CpsD mainly catalyses intermolecular oxidative heterocoupling of two different indole piperazine monomers to generate unexpected 6/5/6/6/6/6/5/6 eight‐ring scaffold via one C‐C bond and two C‐N bonds formation, illuminating its first dimerase role in this family natural products. The proposed catalytic mechanism of CpsD was deeply investigated via diversified substrate derivatization. Moreover, dimeric campesine G shows good insecticidal activity against the global honeybee pest Galleria mellonella. Our work shows a representative example of discovering new skeleton monomeric and dimeric indole piperazine alkaloids from microbial resources, expands our knowledge of bond formation art of CYP450s and supports further development of the newly discovered and engineered campesine family compounds as potential biopesticides.

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Total Synthesis of (−)-Cylindricine H

Cited by 12 publications

References 34 publications

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

Rapid and Efficient Access to Novel Bio-Inspired 3-Dimensional Tricyclic SpiroLactams as Privileged Structures via Meyers’ Lactamization

Marine natural products

A Cytochrome P450 Catalyzes Oxidative Coupling Formation of Insecticidal Dimeric Indole Piperazine Alkaloids

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