A Stereoselective Synthesis of Lentiginosine

Cordero, Franca M.; Vurchio, Carolina; Brandi, Alberto

doi:10.1021/acs.joc.5b02804

Cited by 15 publications

(5 citation statements)

References 28 publications

(25 reference statements)

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“…The reactivity of the elaborated adduct 5 bearing aminal, acetal functions and N–O bonds, was examined by carrying out an acidic treatment . In the presence of a catalytic amount of TFA (10 mol‐%), a complete transformation of 5 occurred within one hour at room temperature.…”

Section: Resultsmentioning

confidence: 99%

High Pressure Elicits Unexpected Transformations of Plain Nitroaromatics with 4‐(Cyclohex‐1‐en‐1‐yl)morpholine

et al. 2018

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An unexpected reaction sequence occurs when simple nitroarenes and the readily available enamine 4‐(cyclohex‐1‐en‐1‐yl)morpholine are placed under high pressure. This one‐pot transformation leads to the generation of highly substituted compounds and presents different advantages such as (1) a rapid increase of molecular complexity through converting simple, cheap, and seldom exploited starting materials into polycyclic structures never described before, (2) the absence of chemical catalysts, (3) a very low energy input.

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Section: Resultsmentioning

confidence: 99%

High Pressure Elicits Unexpected Transformations of Plain Nitroaromatics with 4‐(Cyclohex‐1‐en‐1‐yl)morpholine

et al. 2018

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“…Synthesis of (À )-lentiginosine (ent-4), Cordero and coworkers. [99] lation, and regioselective opening of the aziridine ring, leading to spontaneous cyclization, which afforded piperidone 96. The final steps of this formal synthesis included amide and ester reduction, followed by Boc protection of piperidine nitrogen.…”

Section: Chiral Aziridinesmentioning

confidence: 99%

“…L-(+)-and D-(À )-tartaric acid-derived nitrones 80 and ent-80 were previously successfully used for the preparation of both lentiginosine enantiomers. [97][98] Cordero et al recently reported an improved strategy for the (À )-lentiginosine (ent-4) synthesis, [99] employing stereoselective Grignard addition to nitrone 80, prepared from D-(À )-tartaric acid in 5 steps (Scheme 14). [100] Attack of the bulky Grignard reagent 82 was observed only from less sterically hindered anti-face of the nitrone, leading to hydroxylamine 81 as a single isomer.…”

Section: Tartaric Acidmentioning

confidence: 99%

Recent Developments in the Synthesis of Polyhydroxylated Indolizidines

Fraňová

Marchalı́n

2022

Eur J Org Chem

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Since their discovery, polyhydroxylated indolizidines have been the focus of attention for both biologists and synthetic chemists. They are classified as iminosugar alkaloids: nitrogenbased carbohydrate mimetics that are potent inhibitors of glycosidases. Many discovered glycosidase inhibitors were found to possess biological activity, and they are therefore considered to be potential therapeutics in the treatment of various diseases such as viral infections, diabetes, or cancer. Not surprisingly, the interest in the preparation of these substances has been enormous. This review presents the latest developments in the synthesis of naturally occurring polyhydroxylated indolizidines and their synthetic enantiomers. In addition, the synthesis of several novel polyhydroxylated indolizidines, which were discovered to have inhibitory activity, is reported.

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“…146,147 (−)-Lentiginosine was synthesized from the nitrone derived from D-tartaric acid (Scheme 9). 148 Ukaji and Inomata showed that catalytic asymmetric addition of alkylzinc to 3,4-dihydroisoquinoline N-oxides in the presence of magnesium salt of tartaric acid derivatives gives (S)-1-alkyl-2hydroxy-1,2,3,4-tetrahydroisoquinolines with up to 95% ee (eq 52). 149,150 3.1.1.2.…”

Section: Reaction With Nucleophilesmentioning

confidence: 99%

Synthesis and Transformations of Nitrones for Organic Synthesis

2019

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Nitrones are important compounds and are highly useful in many aspects. The first part describes the methods for synthesis of nitrones, which are useful and environmentally friendly. Catalytic oxidations, condensations, and other useful reactions are described. The nitrones thus obtained are key intermediates for the synthesis of biologically important nitrogen compounds. The second part describes the fundamental transformations of nitrones, which will provide the strategies and means for the construction of nitrogen compounds. The reactions with nucleophiles or radicals, C–H functionalization, and various addition reactions are described. The last reactions are particularly important for highly selective carboncarbon bond formations. 1,3-Dipolar cycloaddition reactions are excluded because the size of the review is limited and excellent reviews have been published in Chemical Reviews.

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A Stereoselective Synthesis of Lentiginosine

Cited by 15 publications

References 28 publications

High Pressure Elicits Unexpected Transformations of Plain Nitroaromatics with 4‐(Cyclohex‐1‐en‐1‐yl)morpholine

High Pressure Elicits Unexpected Transformations of Plain Nitroaromatics with 4‐(Cyclohex‐1‐en‐1‐yl)morpholine

Recent Developments in the Synthesis of Polyhydroxylated Indolizidines

Synthesis and Transformations of Nitrones for Organic Synthesis

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