Asymmetric synthesis of a lignan lactone from a meso anhydride

Ward, Robert S.; Pelter, Andrew; Edwards, Mark I.; Gilmore, Jeremy

doi:10.1016/0040-4020(96)00761-2

Cited by 20 publications

(3 citation statements)

References 19 publications

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“…The overall strategy for building the tribenzylbutyrolactone skeleton of 1 was based on the synthetic route which has been previously reported to the 2,3-aryl di-substituted butyrolactone ring found in lignans (Ward et al, 1995) from higher plants, with the third benzyl unit being introduced by alkylation towards the end of the synthesis. The starting material for the synthesis of maculalactones A-C was 2,3-dibenzylidenesuccinic acid (14), which was prepared from the Stobbe condensation of dimethyl succinate with benzaldehyde (this compound is also commercially available, but rather costly).…”

Section: Synthesis Of Racemic Maculactone Amentioning

confidence: 99%

Chemistry and biology of maculalactone A from the marine cyanobacterium Kyrtuthrix maculans

et al. 2004

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Maculalactone A is the most abundant secondary metabolite in Kyrtuthrix maculans, a marine cyanobacterium found in the mid-high shore of moderately exposed to sheltered rocky shores in Hong Kong and South East Asia. This species appears to survive as 'pure' colonies forming distinct black zones on the rock. Maculalactone A may provide K. maculans with a chemical defense against several marine organisms, including the common grazer, Chlorostoma argyrostoma and settlement by larvae of the barnacles, Tetraclita japonica, Balanus amphitrite and Ibla cumingii. The natural concentration of maculalactone A varied with season and also with tidal height on the shore and although a strong positive linear correlation was observed between maculalactone A concentration and herbivore grazing pressure, manipulative experiments demonstrated that grazing pressure was not directly responsible for inducing the biosynthesis of this metabolite. The potential of maculalactone A as a 'natural' marine anti-fouling agent (i.e. as an alternative to environmentally-damaging copper-and tin-based anti-fouling paints) was investigated after achieving a gram-scale synthesis of this compound. Preliminary field trials with anti-fouling paints which contained synthetic maculalactone A as the active principle have confirmed that this compound seems to have a specific activity against molluscan settlers.

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Section: Synthesis Of Racemic Maculactone Amentioning

confidence: 99%

Chemistry and biology of maculalactone A from the marine cyanobacterium Kyrtuthrix maculans

et al. 2004

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“…The minor isomer cis-4c could also be epimerized to the desired major isomer trans-4c by the reported procedure. [33]…”

Section: Synthesis Of (؎)-Matairesinolmentioning

confidence: 99%

A Novel Approach Towards Dibenzylbutyrolactone Lignans Involving Heck and Radical Reactions: Application to (±)‐Matairesinol Synthesis

Singh

Ghosh

2007

Eur J Org Chem

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“…20 To a solution of substituented (R1, R2 and R3)-benzaldehyde (30 mmole) was added dimethoxytetrahydrofuran (15 mmole), potassium acetate (20 mmole), acetic acid (16 mmole) and water (2 mL). The reaction mixture was refluxed for 12 hours and cooled to room temperature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Ligand Based 3D-QSAR of 2,3-Bis-benzylidenesuccinaldehyde Derivatives as New Class Potent FPTase Inhibitor, and Prediction of Active Molecules

Soung¹,

Kim²,

Kwon³

et al. 2010

Bulletin of the Korean Chemical Society

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In order to search new inhibitors against farnesyl protein transferase (FPTase), a series of 2,3-bis-benzylidenesuccinaldehyde derivatives (1-29) were synthesized and their inhibition activities (pI50) against FPTase were measured. From based on the reported results that the inhibitory activities of dimers 2,3-bis-benzylidenesuccinaldehydes were higher than those of monomers cinnamaldehydes, 3D-QSARs on FPTase inhibitory activities of the dimers (1-29) were studied quantitatively using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis ( The dependence of CoMFA models on chance correlations was evaluated with progressive scrambling analyses. And the inhibitory activity exhibited a strong correlation with steric factors of the substrate molecules. Therefore, from the results of graphical analyses on the contour maps and of predicted higher inhibitory active compounds, it is suggested that the structural distinctions and descriptors that contribute to inhibitory activities (pI50) against FPTase will be able to applied new inhibitor design.

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Asymmetric synthesis of a lignan lactone from a meso anhydride

Cited by 20 publications

References 19 publications

Chemistry and biology of maculalactone A from the marine cyanobacterium Kyrtuthrix maculans

Chemistry and biology of maculalactone A from the marine cyanobacterium Kyrtuthrix maculans

A Novel Approach Towards Dibenzylbutyrolactone Lignans Involving Heck and Radical Reactions: Application to (±)‐Matairesinol Synthesis

Synthesis and Ligand Based 3D-QSAR of 2,3-Bis-benzylidenesuccinaldehyde Derivatives as New Class Potent FPTase Inhibitor, and Prediction of Active Molecules

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