Synthesis of Natural Oxygenated Monocarbocyclic Sesquiterpenoids from 6,7-Epoxygeranyl Acetate

Barrero, Alejandro F.; Álvarez-Manzaneda, Enrique; Chahboun, Rachid; Rivas, Aurea; Palomino, Pérez

doi:10.1016/s0040-4020(00)00560-3

Cited by 22 publications

(13 citation statements)

References 11 publications

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“…OSC inhibitors have been designed and tested as promising candidates for use as antifungal, antitrypanosomal or cholesterol-lowering drugs. Most active among sesquiterpene coumarins were the naturally occurring compound farnesyferol C (IC 50 chemical synthesis [265][266][267][268][269]. A structurally related coumarin, creticacoumarin (144) was isolated by Bohlmann and coworkers from the same source [270].…”

Section: Open-chain Sesquiterpenyloxycoumarinsmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

269

165

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Prenyloxycoumarins and prenyloxyfuranocoumarins (isopentenyloxy-, geranyloxy-, linear and cyclic sesquiterpenyloxy compounds and their biosynthetic derivatives) represent a family of secondary metabolites that have been considered for years just as intermediates of other coumarin-based compounds. Only in the last two decades these secondary metabolites have been recognized as interesting and valuable biologically active natural products. Up to now more than 160 compounds have been isolated from plants mainly belonging to the families of Rutaceae and Umbelliferae, comprising common edible vegetables and fruits like lemons, oranges and grapefruits. In view of the biological activity of some natural prenyloxycoumarins, very recently syntheses of structurally related analogs aimed to establish detailed structure-activity relationships have also been carried out. Many of the isolated prenyloxy- and prenyloxy-furanocoumarins and their semisynthetic derivatives were shown to exert in vitro and in vivo remarkable anti-tumoral, anti-inflammatory and anti-viral effects. The object of this review is to examine in detail the different types of prenyloxycoumarins and prenyloxyfuranocoumarins from the chemical, phytochemical and biological point of view.

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Section: Open-chain Sesquiterpenyloxycoumarinsmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

269

165

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“…This ketol was converted into the single trans-2-carbomethoxy-cyclohexanone (13) by the 1,4 addition of lithium dimethylcuprate, followed by the quenching with methylcyanoformate in HMPA [5]. Treatment of (13) with p-TsOH.H 2 O afforded the crystalline keto-lactone (-)- (14) as a single product. The pathway can be regarded as an acid-induced domino reaction [6] in which the subsequent reaction (cyclization by transesterification) is the result of three reactions (deprotection of (13), epimerization and cyclization).…”

Section: Enantioselective Synthesis Of Both Enantiomers Of Karahana Lmentioning

confidence: 99%

“…In 1996, Marco et al [12] isolated two new monocyclic sesquiterpenes (4) and (5) from the aerial parts of Artemisia chamaemelifolia ssp. Since then, only one racemic synthesis of (4) has been published [13]. 4).…”

Section: Enantioselective Synthesis Of Two Monocyclic Sesquiterpenes mentioning

confidence: 99%

Lipases-Promoted Enantioselective Syntheses of Monocyclic Natural Products

Monti¹,

Audran²

2005

MROC

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“…The mechanism postulated for this cyclization (Figure 3) is shown in Figure 3. Equilibrium between compounds 5-6 and the monocyclic carbocation intermediate I allow their isomerization toward the target 2, thus increasing its yield with longer reaction times [10].…”

mentioning

confidence: 99%