NIS–PPh<sub>3</sub>: A Selective Reagent for the Spiroannulation of <i>o</i>-Allyl Phenols. Total Synthesis of Corallidictyal D

Caño, María José; Bouanou, Hanane; Tapia, Rubén; Alvarez, Esteban; Álvarez-Manzaneda, Ramón; Chahboun, Rachid; Álvarez-Manzaneda, Enrique

doi:10.1021/jo4014047

Cited by 30 publications

(23 citation statements)

References 37 publications

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“…Very recently, our group reported the preparation of spirodihydrobenzofuran derivatives by the cyclization of o-allyl phenols mediated by NIS-PPh 3 . 15 The I 2 -PPh 3 mediated spirocyclization of unsaturated β-dicarbonyl compounds, with complete regio-and stereoselectivity, was also communicated very recently by the present authors. 16…”

Section: Introductionsupporting

confidence: 58%

The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

et al. 2014

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A very efficient method for synthesizing spirolactones is reported. Treatment of δ,ε-unsaturated carboxylic acids with iodine and triphenylphosphine under mild conditions leads to the corresponding spiro γ-lactones in high yield and with complete stereoselectivity. Utilizing this, the first synthesis of the terpene spirolactones (-)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B has been achieved.

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Section: Introductionsupporting

confidence: 58%

The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

et al. 2014

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“…Chemical demethylenation of corynoline was performed, based on a published protocol (Cano et al, 2013). Briefly, corynoline (2 mg) and AlCl 3 (2.2 mg) were mixed in 4 ml of toluene.…”

Section: Methodsmentioning

confidence: 99%

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

2015

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Corynoline is a 1,3-benzodioxole-containing isoquinoline alkaloid isolated from Corydalis bugeana Turcz., a traditional herbal medicine. Corynoline has reportedly demonstrated multiple pharmacologic properties. Previous studies have also shown that corynoline induced cytotoxicity and inhibited cytochrome P450 (CYP) enzymes, but the mechanisms of the adverse effects remain unknown. The major objective of the present study was to identify reactive metabolites of corynoline responsible for the cytotoxicity and enzyme inhibition. Three oxidative metabolites (M1-M3) were detected by liquid chromatography-tandem mass spectrometry in rat liver microsomal incubations after exposure to corynoline. M1 and M2 were two isomers of catechol derivatives, and M3 was a dicatechol. The M1-M3 metabolites were also observed in urine of rats given corynoline. A total of four N-acetylcysteine (NAC) conjugates (M4-M7) were detected in microsomes containing corynoline, NAC, and NADPH. Apparently, M4 and M5 were derived from M1, M6 resulted from M2, and M7 was a M3-derived NAC conjugate. This indicates that corynoline was bioactivated to ortho-quinone derivatives. No corynoline-derived NAC conjugates (M4-M7) were detected in urine of rats given corynoline; however, three corresponding cysteinylglycine conjugates (M8-M10) were observed instead. Recombinant P450 enzyme incubations demonstrated that the CYPs 2C9, 3A4, and 2C19 were mainly involved in metabolic activation of corynoline. The metabolism study facilitates the understanding of corynoline-induced cytotoxicity and P450 enzyme inhibition.

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“…[29b] Stachybotrylactam, an spirodihydrobenzofuranlactam active as antagonist of endothelin and as inhibitor of HIV-1 protease, [30] isolated from the cultures of two different Stachybotrys species, [31] and various other analogous have also been synthesized using the cationic resin as the cyclizing agent. [32] An interesting Niodosuccinimide-triphenylphosphine (NIS-PPh 3 ) system, as a selective reagent for the spiroannulation reaction was introduced for the total synthesis of Corallidictyal D, [33] a spirosesquiterpene aldehyde isolated from the marine sponge Aka coralliphaga with protein kinase inhibitory activity. [34] Using the same system ( À )-F1839-I and Corallidictyal B and C were also successfully synthesized [35,36] (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective Synthesis of Spirodihydrobenzofuran Analogues of the Natural Product Filifolinol

et al. 2020

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Filifolinol is a natural occurring spirodihydrobenzofuran isolated from the resinous exudates of Heliotropium filifolium, a Chilean endemic shrub. Filifolinol and some of its derivatives have shown interesting biological activities against pathogens that attack salmonid species. Whereas the synthesis of spirodihydrobenzofurans has been limited to the use of an ortho allylphenol unit herein we report a different approach based on a C−H activation/C−O cyclization reaction for the synthesis of analogues of Filifolinol. Moreover, a diastereoselective approach was developed using the different facial preference of hydride species and organolithium compounds towards cyclic ketones.

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NIS–PPh₃: A Selective Reagent for the Spiroannulation of o-Allyl Phenols. Total Synthesis of Corallidictyal D

Cited by 30 publications

References 37 publications

The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

Diastereoselective Synthesis of Spirodihydrobenzofuran Analogues of the Natural Product Filifolinol

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NIS–PPh3: A Selective Reagent for the Spiroannulation of o-Allyl Phenols. Total Synthesis of Corallidictyal D

Cited by 30 publications

References 37 publications

The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

Diastereoselective Synthesis of Spirodihydrobenzofuran Analogues of the Natural Product Filifolinol

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NIS–PPh₃: A Selective Reagent for the Spiroannulation of o-Allyl Phenols. Total Synthesis of Corallidictyal D