Efficient Synthesis of a New L-Shaped Dimer of Naphthalene, and Its Analogs

Yoshioka, Ken; Takaishi, Izumi; Shiozawa, Kazunari; Fukushi, Yukiharu; Tahara, Satoshi

doi:10.1271/bbb.80306

Cited by 3 publications

(1 citation statement)

References 14 publications

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“…Nevertheless, extensive work has been directed towards benzannulated spiroketal model systems using novel spirocyclisation methodology, with elegant new developments including alkoxyselenation, 6 alkyne cyclotrimerization, 7 glycoside rearrangement, 8 Michael additions, 9,10 ring-closing metathesis, 11 o-quinone methide hetero-Diels-Alder cycloadditions, [12][13][14] [3 + 2]-dipolar cycloadditions, 15,16 alkyne hydroalkoxylations, 17,18 radical cyclisation, 19 lactone alkylidenation, 20 palladium(II)-catalysed one-pot multi-component cascade reactions, 21 ring expansion of donor-acceptor substituted cyclopropanes, 22 kinetic spirocyclisation of glycal epoxides 23 and an intramolecular Ullman-ether reaction. 24 2 5,5-Spiroketals…”

Section: Introductionmentioning

confidence: 99%

Isolation, biological activity and synthesis of benzannulated spiroketal natural products

et al. 2010

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Section: Introductionmentioning

confidence: 99%

Isolation, biological activity and synthesis of benzannulated spiroketal natural products

et al. 2010

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Synthesis of Phenyl‐1‐benzoxepinols Isolated from Butcher's Broom and Analogous Benzoxepines

et al. 2014

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Extracts of Ruscus aculeatus L., known as butcher's broom, are mainly used for the treatment of chronic venous insufficiency (CVI). In a recent study on the phenolic compounds of Rusci rhizoma, new phenyl‐1‐benzoxepinols were isolated. As the therapeutic effect of butcher's broom is ascribed to the pharmacological activity of the main constituents, steroidal saponins and their aglycones the ruscogenins, the role of the newly identified compounds was of interest. Owing to the low availability of the compounds by isolation, we synthesized them for pharmacological testing. In an ORAC–fluorescein assay they revealed a significant antioxidative activity, which may contribute to the anti‐inflammatory properties of the phenolic fraction obtained from Rusci rhizoma extracts.

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Solvent-Dependent Divergent Functions of Sc(OTf)₃ in Stereoselective Epoxide-Opening Spiroketalizations

2014

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A stereocontrolled synthesis of benzannulated spiroketals has been developed using solvent-dependent Sc(OTf)3-mediated spirocyclizations of exo-glycal epoxides having alcohol side chains. In THF, the reaction proceeds via Lewis acid catalysis under kinetic control with inversion of configuration at the anomeric carbon. In contrast, in CH2Cl2, Brønsted acid catalysis under thermodynamic control leads to retention of configuration. The reactions accommodate a variety of aryl substituents and ring sizes and provide stereochemically diverse spiroketals.

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Efficient Synthesis of a New L-Shaped Dimer of Naphthalene, and Its Analogs

Cited by 3 publications

References 14 publications

Isolation, biological activity and synthesis of benzannulated spiroketal natural products

Isolation, biological activity and synthesis of benzannulated spiroketal natural products

Synthesis of Phenyl‐1‐benzoxepinols Isolated from Butcher's Broom and Analogous Benzoxepines

Solvent-Dependent Divergent Functions of Sc(OTf)₃ in Stereoselective Epoxide-Opening Spiroketalizations

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Efficient Synthesis of a New L-Shaped Dimer of Naphthalene, and Its Analogs

Cited by 3 publications

References 14 publications

Isolation, biological activity and synthesis of benzannulated spiroketal natural products

Isolation, biological activity and synthesis of benzannulated spiroketal natural products

Synthesis of Phenyl‐1‐benzoxepinols Isolated from Butcher's Broom and Analogous Benzoxepines

Solvent-Dependent Divergent Functions of Sc(OTf)3 in Stereoselective Epoxide-Opening Spiroketalizations

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Solvent-Dependent Divergent Functions of Sc(OTf)₃ in Stereoselective Epoxide-Opening Spiroketalizations