Synthesis of (±)-Crispine A via a Nitrosoalkene Hetero-Diels-Alder Addition to Ethyl Vinyl Ether

Yioti, Efthymia G.; Mati, Ioulia K.; Arvanitidis, Athanasios G.; Massen, Zoe S.; Alexandraki, Elli S.; Gallos, John K.

doi:10.1055/s-0030-1258333

Cited by 11 publications

(2 citation statements)

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“…7 Due to its importance, a stereoselective synthesis of sacubitril remains a challenge; thus, we considered a new, totally different approach to intermediate lactam 8, depicted in Scheme 1. Target compound 8 could be prepared from oxazinane derivative 9 by reductive ring contraction, which in turn is a stereoselective reduction product of dihydrooxazine 10, a hetero-Diels-Alder adduct of ethyl 2-nitrosoacrylate (12) to enol ether 11.…”

Section: Feature Synthesismentioning

confidence: 99%

“…9 Previously, we have studied the conversion of substituted ethyl 6-alkoxy-5,6-dihydro-4H-1,2-oxazine-3-carboxylates (such as 10, Scheme 1) into several interesting products, such as nonnatural amino acids, 10 aza-sugars 11 and alkaloids. 12 The applicability of these reactions is further broadened by their potential asymmetric versions. 9 Usually, a chiral enol ether is used, prepared from the respective chiral alcohol, and adducts are formed with acceptable to high diastereoselectivity.…”

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Hetero-Diels–Alder Addition of Ethyl 2-Nitrosoacrylate to (Z)-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril

Zisopoulou

Andreou²,

Koftis

et al. 2023

Synthesis

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A novel, conceptually distinct, synthesis of a key precursor to sacubitril, an antihypertensive drug, is presented. The well-demonstrated hetero Diels-Alder addition of in situ generated nitroso alkenes to electron rich enol ethers is engaged to establish the required functionalities with controllable relative stereochemistry. An asymmetric variant of the enol ether enables the access to the target molecule in enantiopure form.

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confidence: 99%

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confidence: 99%

Hetero-Diels–Alder Addition of Ethyl 2-Nitrosoacrylate to (Z)-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril

Zisopoulou

Andreou²,

Koftis

et al. 2023

Synthesis

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Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A

et al. 2021

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As a naturally occurring small-molecule, various optical isomers of chiral pyrrolo[2,1-a]isoquinoline alkaloid crispine A represent a potential class of chiral molecules in contemporary organic chemistry, and possess diverse biological activities. The range of pharmacological activities include antidepressant, antiplatelet, antileukemic, and anticancer activities. This review provides an overview of the literature on the strategies, employed in the synthesis of crispine A in their racemic and enantiopure forms via Bischler-Napieralski cyclization, Pictet-Spengler cyclization, N-Alkylation/Acylation-cyclization, Oxidative cyclization, and Asymmetric hydrogenation in the period of 1931-2021. This study accentuates the need for the developing more effective synthesis, and search for involved biological applications for the pyrroloisoquinoline class of natural product. Attention has been drawn towards the use of relatively less documented but easily accessible naturally occurring diastereomeric scaffolds namely, garcinia and hibiscus acids. These lactones obtained from (+)and (À )-2-hydroxycitric acids bearing chemically amenable functional groups are investigated as an ideal choice for the enantiopure synthesis of the (À )-(R)-and (+)-(S)-Crispine A structural frame work.

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Green synthesis and investigation of antioxidant ability new pyrazines containing pyrrolo[2,1‐a]isoquinolines derivatives

Moghaddas

Hossaini

Zareyee

2020

Journal of Heterocyclic Chem

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In this study, a new, easy and high yield procedure is investigated for the generation of pyrazine containing pyrrolo[2,1‐a]isoquinoline derivatives using multicomponent reaction of phthalaldehyde or its derivatives, primary amines, α‐haloalketones, electron deficient acetylenic compounds, ammonium acetate and KF/Clinoptilolite nanoparticles (KF/CP NPs) as catalyst in water at room temperature. The reactions of 2‐hydroxy phthalaldehyde, primary amines, α‐haloketones, electron deficient acetylenic compounds, and ammonium acetate in the presence of KF/CP NPs as catalyst in water at room temperature produce pyrazine derivatives in good yields. Also, in this work, antioxidant ability was studied for a number of prepared compounds employing the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical scavenging and power of compounds for reducing of ferric ion experiments and evaluating results with synthetic antioxidants (TBHQ and BHT). Comfortable, simple, fast and fresh procedure is the advantages of this study.

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Synthesis of (±)-Crispine A via a Nitrosoalkene Hetero-Diels-Alder Addition to Ethyl Vinyl Ether

Cited by 11 publications

References 1 publication

Hetero-Diels–Alder Addition of Ethyl 2-Nitrosoacrylate to (Z)-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril

Hetero-Diels–Alder Addition of Ethyl 2-Nitrosoacrylate to (Z)-Prop-1-enyl Ethers. Stereoselective Synthesis of a Precursor to Sacubitril

Synthesis of Pyrrolo[2,1‐a]isoquinoline Class of Natural Product Crispine A

Green synthesis and investigation of antioxidant ability new pyrazines containing pyrrolo[2,1‐a]isoquinolines derivatives

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