Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins

Ogiku, Tsuyoshi; Yoshida, S.; Ohmizu, Hiroshi; Iwasaki, Tameo

doi:10.1021/jo00119a041

Cited by 46 publications

(12 citation statements)

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“…Trifluoromethanesulfonic anhydride (225 mg, 0.80 mmol) was added dropwise, and the mixture was warmed to room temperature. [23] The mixture was then diluted with Et 2 O, and the reaction was quenched with the addition of HCl (1 N solution).…”

Section: -[(Tert-butoxycarbonyl)oxy]-67-dimethoxy-3-oxo-13-dihydromentioning

confidence: 99%

“…After filtration, the solvent was removed under reduced pressure, and the crude residue was purified by column chromatography (hexane/ethyl acetate, 3:1) to afford 14 ( [23] Chinensinaphthol (16): To a solution of 14 (42.8 mg, 0.087 mmol), Pd(OAc) 2 (2.0 mg, 0.009 mmol), PCy 3 (4.9 mg, 0.017 mmol), and Cs 2 CO 3 (85.0 mg, 0.26 mmol) in 25 % aqueous 1,4-dioxane (0.87 mL, 0.1 M) was added potassium 1,3-benzodioxol-5-yltrifluoroborate (31.8 mg, 0.13 mmol). Trifluoromethanesulfonic anhydride (613 mg, 2.17 mmol) was added dropwise, and the mixture was warmed to room temperature.…”

Section: -[(Tert-butoxycarbonyl)oxy]-6-oxo-68-dihydrofuro[3′4′:67mentioning

confidence: 99%

“…136.3-137.8°C. 1 [23] Chinensinaphthol (16): To a solution of 14 (42.8 mg, 0.087 mmol), Pd(OAc) 2 (2.0 mg, 0.009 mmol), PCy 3 (4.9 mg, 0.017 mmol), and Cs 2 CO 3 (85.0 mg, 0.26 mmol) in 25 % aqueous 1,4-dioxane (0.87 mL, 0.1 M) was added potassium 1,3-benzodioxol-5-yltrifluoroborate (31.8 mg, 0.13 mmol). The mixture was stirred at 120°C for 17 h, and the reaction was then quenched with a saturated solution of NH 4 Cl.…”

Section: -[(Tert-butoxycarbonyl)oxy]-6-oxo-68-dihydrofuro[3′4′:67mentioning

confidence: 99%

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An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

et al. 2017

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A simple method for the preparation of arylnaphthalene lactone natural products was developed and used to synthesize diphyllin (10), justicidin A (12), cilinaphthalide B (13), taiwanin E (15), chinensinaphthol (16), taiwanin E methyl ether (17), chinensinaphthol methyl ether (18), justicidin C (21), and justicidin D (22). Key steps of the syntheses include the Hauser–Kraus annulation of cyanophthalides 7a and 7b and Suzuki–Miyaura cross‐coupling reactions between arylnaphthalene lactones that contain a sulfonate group (i.e., 9, 14, 19, and 20) and various potassium aryltrifluoroborates.

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Section: -[(Tert-butoxycarbonyl)oxy]-67-dimethoxy-3-oxo-13-dihydromentioning

confidence: 99%

Section: -[(Tert-butoxycarbonyl)oxy]-6-oxo-68-dihydrofuro[3′4′:67mentioning

confidence: 99%

Section: -[(Tert-butoxycarbonyl)oxy]-6-oxo-68-dihydrofuro[3′4′:67mentioning

confidence: 99%

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An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

et al. 2017

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“…Retrosynthetically, 1 and 2 can be logically disconnected into two fragments: diphyllin and the sugar residues, which were linked by a β-glycosidic bond. Syntheses of diphyllin have been reported by several groups, 13,14 thus, choosing a suitable glycosylation strategy became the key step to our syntheses. The bad solubility of diphyllin in most organic solvents (only soluble in acetone and DMSO) made its glycosylation a difficult task under acid promoted conditions.…”

Section: Resultsmentioning

confidence: 99%

First Synthesis of Bioactive Diphyllin Glycosides Isolated from Justicia patentiflor Hemsl

Zhao

Li²

2007

Chin. J. Chem.

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The syntheses of three naturally occurring diphyllin glycosides have been achieved. 7-O-β-D-Quinovopyranosyldiphyllin (patentiflorin A) and 7-O-β-L-fucopyranosyldiphyllin (patentiflorin B) were synthesized by the glycosylation of diphyllin with peracetylglycosyl bromides under phase transfer catalysis (PTC) conditions. 4"-O-Acetyl-7-O-β-L-fucopyranosyldiphyllin (4"-O-acetyl patentiflorin B) was obtained from patentiflorin B on an orthoesterification-orthoester rearrangement approach. Their 1 H NMR, 13 C NMR and HRMS signals are all consistent with those reported for the natural product.

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“…Photo-assisted cyclization methods provide arylnaphthalene lignan lactones efficiently (Block and Stevenson, 1971 , 1973 ; Arnold et al, 1973 ; Yamamoto et al, 2015 ). Tandem conjugate addition-aldol reaction protocol (Ogiku et al, 1990 ; Kamal et al, 1994 ), benzoin condensation-thermal cyclization (Hayat et al, 2015 ), and electrophilic aromatic substitution protocols (González et al, 1978 ; Ogiku et al, 1995 ) have also been reported. Recently, synthetic approaches and biological activities of arylnaphthalene lignan lactones were reviewed by Zhao et al ( 2018 ).…”

Section: Introductionmentioning

confidence: 99%

Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

Park

Kim

et al. 2020

Front. Chem.

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Arylnaphthalene lignan lactones belong to a class of natural lignans, and more than 60 analogs have been isolated. Their pharmacological activities as well as unique structural features have attracted considerable attention from medicinal and synthetic chemists. Since the first synthesis in 1895, many synthetic methodologies with ionic or pericyclic reaction mechanisms have been reported. Transition metal catalysts sometimes provide exceptional synthetic versatility for the syntheses of natural compounds. Recently, transition metal-mediated methodologies were investigated for the construction of basic scaffolds of arylnaphthalene lignan lactones. Five kinds of transition metal catalysts containing gold, manganese, nickel, palladium, and silver have been explored. Most of the metal catalysts successfully created arylnaphthalene lactones by intermolecular or intramolecular annulative cyclization. In this review, all reports of transition metal-mediated annulative construction of arylnaphthalene lignan lactones were compiled, and synthetic approaches, mechanistic aspects, and successful applications were discussed.

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Efficient Syntheses of 1-Arylnaphthalene Lignan Lactones and Related Compounds from Cyanohydrins

Cited by 46 publications

References 1 publication

An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

First Synthesis of Bioactive Diphyllin Glycosides Isolated from Justicia patentiflor Hemsl

Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

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