Total Synthesis of (+)‐Hyacinthacine A<sub>2</sub> (I) Based on SmI<sub>2</sub>‐Induced Nitrone Umpolung.

Desvergnes, Stéphanie; Py, Sandrine; Vallée, Yannick

doi:10.1002/chin.200530177

Cited by 4 publications

(5 citation statements)

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“…Lower or higher syngas pressures always led to worse results in terms of yield of compound 22 . Hydrogenolysis of 21 or 22 over Pd/C has been previously reported to give hyacinthacine A 2 ( 1 ) [ 15 , 51 , 52 , 53 ] and is here used together with MW irradiation. Moreover, as we worked in a very small scale, the final product was obtained in such a low amount that good quality NMR spectra could not be recorded.…”

Section: Resultsmentioning

confidence: 99%

“…: 49–51 °C Lit. [ 52 ] 47.5 °C ES-MS: 444 [M+H] + . 1 H-NMR (400 MHz, CDCl 3 ): δ 7.30–7.25 (m, 15H, Ar H ), 4.66 (d, J = 11.6 Hz, 1H, OC H 2 Ph); 4.67–4.49 (m, 5H, OC H 2 Ph), 4.04 (t, J = 7.2 Hz, 1H, 3-C H ), 3.78 (t, J = 7.2 Hz, 1H, 3-C H ), 3.56–3.45 (m, 3H, 1- H , 2- H , 7a- H ), 3.10–3.03 (m, 1H, 3-C H ), 3.00–2.92 (m, 1H, 5-C H ), 2.81 – 2.72 (m, 1H, 5- H ), 1.99 – 1.57 (m, 4H, 6-C H 2 , 7-CH 2 ) ppm.…”

Section: Methodsmentioning

confidence: 99%

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An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

et al. 2022

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A general method for the synthesis of pyrrolizidine derivatives using an intramolecular hydroaminomethylation protocol (HAM) under microwave (MW) dielectric heating is reported. Starting from a 3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-vinylpyrrolidine, MW-assisted intramolecular HAM in the presence of gaseous H2 and CO gave the natural alkaloid hyacinthacine A2 protected as benzyl ether. The same approach gave a lentiginosine analogue starting from the corresponding vinyl N-hydroxypyrrolidine. The nature of the reaction products and the yields were strongly influenced by the relative stereochemistry of the starting pyrrolidines, as well as by the catalyst/ligand employed. The use of ethanol as a solvent provides environmentally friendly conditions, while the ligand/catalyst system can be recovered by separating the alkaloid product with an SCX column and recycling the ethanolic solution. HAM worked up to three times with the recycled catalyst solution without any significant impact on yield.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

et al. 2022

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“…They possess glycosidase inhibitory activity of rat intestine lactase (IC 50 =4.4-μM), L-fucosidase (IC 50 =46 μM), and amyloglucosidase (IC 50 =25 μM) [38][39][40][41]. Hyacinthacines A 1 , A 2 , A 3 , and B 3 can be obtained by various synthetic pathways [42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60].…”

Section: Resultsmentioning

confidence: 99%

Muscari Armeniacum Leichtlin (Grape Hyacinth): Phytochemistry and Biological Activities Review

Bokov

2019

Asian J Pharm Clin Res

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This review focuses on the Muscari armeniacum Leichtlin (Asparagaceae Juss) biologically active substances composition presented in the Aireal and underground parts and finding their possible therapeutic effects. The systematic review is dedicated to the composition of biologically active substances, including recent advances in the biological activity investigation, phytochemical studies, and biotechnology methods of plant material producing. Various electronic search engines such as Google, Google Scholar, scientific literature, publishing sites, and electronic databases such as PubMed, Wiley, Springer, and Science Direct had been searched and data obtained. Other online academic libraries such as E-library and specific ethnopharmacological literature had been searched systematically for more exhaustive information on the crude herbal drug. The chemical composition of M. armeniacum biologically active substances is established; it contains anthocyanins (delphinidin and cyanidin derivatives), homoisoflavonoids, polyhydroxylated pyrrolizidine alkaloids (hyacinthacines A1, A2, A3, and B3), oligoglycosides (Muscarosides), and ribosome-inactivating proteins (musarmins). Recent physicochemical analytical procedures for components determination and hyacinthacines synthesis pathways are mentioned. Moreover, future prospects and trends in the research of this plant have been proposed. We have reviewed researches conducted on M. armeniacum especially in areas of its use in medicine, phytochemicals, biological activity, and developed analytical methods. M. armeniacum possesses antioxidant, antimutagenic activity, and specific glycosidase inhibitory activity; M. armeniacum can be used for the production of potential anticancer, antiviral, antidiabetic, and anti-obesity drugs. It should be noted that more pharmacognostic, pharmacological studies are needed for giving further information on the clinical practice and standardization procedures for the crude herbal drug.

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“…Compound 90 was used for the synthesis of (+)-hyacinthacine A 2 (Scheme 29). [106] The same reaction with substituted ethyl acrylate 89, but in the presence of 12 equiv. of lithium bromide, afforded hydroxylamine 91 which was reduced in situ en route to (+)-australine.…”

Section: Scheme 25mentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

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This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of carbanions derived from enolates, cyanide or fluorinated derivatives allow the preparation of complex structures. Radical additions and, in particular samarium diiodide-mediated reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamienes that are valuable synthetic intermediates. KeywordsHydroxylamines; Nitrones; Organometallics; Mannich; Reductive coupling 2 Graphical Abstract 3

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Total Synthesis of (+)‐Hyacinthacine A₂ (I) Based on SmI₂‐Induced Nitrone Umpolung.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 4 publications

References 1 publication

An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

Muscari Armeniacum Leichtlin (Grape Hyacinth): Phytochemistry and Biological Activities Review

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

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Total Synthesis of (+)‐Hyacinthacine A2 (I) Based on SmI2‐Induced Nitrone Umpolung.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 4 publications

References 1 publication

An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

An Intramolecular Hydroaminomethylation-Based Approach to Pyrrolizidine Alkaloids under Microwave-Assisted Heating

Muscari Armeniacum Leichtlin (Grape Hyacinth): Phytochemistry and Biological Activities Review

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

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Total Synthesis of (+)‐Hyacinthacine A₂ (I) Based on SmI₂‐Induced Nitrone Umpolung.