Naturally Occurring 5-Lipoxygenase Inhibitors. VII. Practical Synthesis of Ardisiaquinones D, E and F.

Kiriyama, Yuuko; Kodama, Masashi

doi:10.1248/cpb.46.1770

Cited by 8 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 1995, Fukuyama et al 86 reported the isolation of ardisiquinone D-F (78-80) from the same species and later published their total synthesis. 87 In 2001, Yang et al 88 extended the series to isolate ardisiaquinones G-I (81-83) from the leaves of Ardisia teysmanniana. All these quinones showed antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

View full text Add to dashboard Cite

As 1,4-benzoquinonas são encontradas em toda a natureza, podendo ser sintetizadas por diversas estratégias. Esta revisão apresenta os desenvolvimentos recentes das metodologias de síntese, das reações de ciclo adição, da química computacional e dos estudos de pulso radiolítico. Destaca ainda a sua significância química e biológica e de seus compostos derivados.1,4-Benzoquinones are ubiquitous in nature and can be synthesized by diverse strategies. Recent developments on their synthetic methodologies, cycloaddition reactions, computational chemistry and pulse radiolytic studies are reported in this review. Their chemical and biological significance as well as their derivates' are also covered.

show abstract

Section: Introductionmentioning

confidence: 99%

Recent advances in 1,4-benzoquinone chemistry

Abraham¹,

Joshi²,

Pardasani³

et al. 2011

J. Braz. Chem. Soc.

165

View full text Add to dashboard Cite

show abstract

“…Our initial attempts to perform this displacement in a direct way, by reacting 66b with hydroxide anion, led to formation of multiple products, arising presumably by reaction of hydroxide anions at both the C18 and C21 centers. This problem was circumvented by using a two-step procedure that involved reaction of 66b with sodium methoxide at elevated temperature (3 equiv of sodium methoxide at 50 °C) to furnish dimethoxyquinone 67 , followed by selective hydrolysis of the C21 methoxy unit under dilute perchloric acid conditions. , This sequence of reactions gave rise to synthetic ilimaquinone ( 6 ) in 56% overall yield . Finally, exposure of 6 to phenylethylamine under basic conditions afforded synthetic smenospongidine ( 7 ) in 91% yield (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Unified Synthesis of Quinone Sesquiterpenes Based on a Radical Decarboxylation and Quinone Addition Reaction

et al. 2002

View full text Add to dashboard Cite

A unified synthesis of several quinone sesquiterpenes is described herein. Essential to this strategy is a novel radical addition reaction that permits the attachment of a fully substituted bicyclic core 16 to a variably substituted quinone 10. The addition product 15 can be further functionalized, giving access to natural products with a high degree of oxygenation at the quinone unit. The quinone addition reaction is characterized by excellent chemoselectivity, taking place only at conjugated and unsubstituted double bonds, and regioselectivity, being strongly influenced by the resonance effect of heteroatoms located on the quinone ring. These features were successfully applied to the synthesis of avarol (1), avarone (2), methoxyavarones (4, 5), ilimaquinone (6), and smenospongidine (7), thereby demonstating the synthetic value of this new method.

show abstract