An Efficient Synthesis of Thalifoline

Youchu, Wang; Georghiou, Paris E.

doi:10.1055/s-2002-34844

Synthesis

2002

DOI: 10.1055/s-2002-34844

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An Efficient Synthesis of Thalifoline

Wang Youchu¹,

Paris E. Georghiou²

Abstract: An efficient multi-step approach for the synthesis of the isoquinolin-1-one alkaloid thalifoline (1) is described. The key intermediate carbamate 8a underwent a modified Bischler-Napieralski-type cyclization using Banwell's Tf 2 O/DMAP conditions to form the lactam 9a under mild conditions and in excellent yield.

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Cited by 5 publications

References 13 publications

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Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

De-la-Cruz-Chacón

Riley‐Saldaña

Arrollo‐Gómez

et al. 2019

Chemistry & Biodiversity

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Annona purpurea grows in the areas of low elevation in deciduous forests of Mexico, those areas have marked rainy and dry seasons. This species produces more than 30 bioactive alkaloids that could have potential in the control of phytopathogens. This research provides data on the variation of the content and number of alkaloids during an annual cycle and the associated inhibitory potential of the compounds against three phytopathogenic fungi. For one year, alkaloidal extracts of stems and leaves were obtained every two months. The extract profiles were determined by gas chromatography with tandem mass spectrometry and their antifungal activity was examined in vitro. The alkaloids, annomontine and oxopurpureine, obtained from the roots and leaves, respectively, were also evaluated individually. The yields, profiles and activities of the extracts, as well as the abundance of annomontine and oxopurpureine in the extracts, were contrasted with the seasonality and phenological phases of the plant. The data indicate that the alkaloid content was higher at the height of the dry season. High yields also occurred during flowering. The strongest inhibitory effect was obtained from the root extracts during the last month of dry season. This finding seems to be explained by the higher chemodiversity of alkaloids in extracts from this season. Annomontine and oxopurpureine inhibited all three phytopathogens; however, they were not solely responsible for the activity of A. purpurea.

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Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

De-la-Cruz-Chacón

Riley‐Saldaña

Arrollo‐Gómez

et al. 2019

Chemistry & Biodiversity

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Green Synthesis of 3,4‐Unsubstituted Isoquinolones through Rhodium(III)‐Catalyzed C−H Activation and Annulation in Ethanol

Kumar,

Gandeepan

2023

Eur J Org Chem

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A mild and convenient synthesis of 3,4‐unsubstituted isoquinolones has been achieved from N‐methoxybenzamides and vinylene carbonate as an acetylene surrogate with a versatile rhodium(III) catalyst. The reaction proceeded at room temperature in biomass derived ethanol solvent. This protocol avoids the use of stoichiometric external oxidant, as the vinylene carbonate served as the internal oxidant. The C‒H/N‒H activation and annulation manifold proceeded with broad substrate scope and excellent levels of regioselectivities. The preliminary mechanistic studies suggest facile and reversible chelation‐assisted C‒H rhodation. Diversification of 3,4‐unsubstituted isoquinolones provide access to 4‐substituted isoquinolones and 3,4‐unsubstituted isoquinolines, which are complementary to the previously reported protocols.

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Domino ring opening and selective O/S-alkylation of cyclic ethers and thioethers

et al. 2020

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An Efficient Synthesis of Thalifoline

Cited by 5 publications

References 13 publications

Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

Green Synthesis of 3,4‐Unsubstituted Isoquinolones through Rhodium(III)‐Catalyzed C−H Activation and Annulation in Ethanol

Domino ring opening and selective O/S-alkylation of cyclic ethers and thioethers

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