Synthesis of certain n-butyltetra- and hexa-hydrophthalides

Cocker, Wesley; McMurry, T. Brian H.; Sainsbury, D. M.

doi:10.1039/j39660001152

Cited by 8 publications

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“…Relative configurations of the cis-ring-configured 3-butylhexahydrophthalides were described by , Cocker et al (1966), andManzardo et al (1996). Very recently, the stereoselective analysis of all eight 3-butylhexahydrophthalides has been realized (Bartschat et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

Stereoisomeric Flavor Compounds. 79. Simultaneous Enantio- selective Analysis of 3-Butylphthalide and 3-Butylhexahydro- phthalide Stereoisomers in Celery, Celeriac, and Fennel

Bartschat

Beck

Mosandl

1997

J. Agric. Food Chem.

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Using enantioselective multidimensional gas chromatography with heptakis[2,3-di-O-acetyl-6-O-(tert-butyldimethylsilyl)]-β-cyclodextrin as the chiral stationary phase, the simultaneous analysis of the 3-butylphthalide enantiomers and all eight 3-butylhexahydrophthalide stereoisomers was achieved. Enantiomeric distributions of compounds in celery, celeriac, celery seed, and fennel extracts were elucidated. Keywords: Enantioselective multidimensional gas chromatography (enantio-MDGC); 3-butyl(hexahydro)phthalide stereoisomers; celery; celeriac; fennel

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Section: Introductionmentioning

confidence: 99%

Stereoisomeric Flavor Compounds. 79. Simultaneous Enantio- selective Analysis of 3-Butylphthalide and 3-Butylhexahydro- phthalide Stereoisomers in Celery, Celeriac, and Fennel

Bartschat

Beck

Mosandl

1997

J. Agric. Food Chem.

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Stereoisomeric flavor compounds LXXVII: 3‐Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers

Bartschat

Wüst

Mosandl

et al. 1997

J. High Resol. Chromatogr.

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SummaryUsing heptakis-(2,3-di-0-acetyl-6-0-tert-butyldimethy~ilyl)-~-cyclodextrin as the chiral stationary phase in enantioselective gas chromatography, the simultaneous enantioselective analysis of all eight 3-hutylhexahydrophthalide stereoisomers was achieved. Furthermore, the odor characteristics and odor thresholds were investigated by enantioselective gas chromatography/olfactometry. Racemic standards were synthesized via hydrogenation and subsequent base catalyzed epimerization, starting from racemic 3-butylphthalide. After separation by high performance liquid chromatography, relative configurations of the pure diastereoisomers were determined by means of NOE-difference spectroscopy. The absolute configuration at C-3 was determined starting from (3s)-butylphthalide as an educt for hydrogenation and epimerization. Absolute configurations of all eight 3-butylhexahydrophthalide stereoisomers are unambiguously concluded from the NOE-experiments in connection with the determination of the absolute configuration at (2-3.

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Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity

León

Del-Ángel

Ávila

et al. 2017

Progress in the Chemistry of Organic Natural Products

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Phthalides are a relatively small group of natural compounds confined to several plant families and some genera of fungi and liverworts. They are divided into two structural groups, the monomeric and dimeric phthalides, and known mainly as bioactive constituents of different plant species used traditionally for medicinal purposes in Asia, Europe, and North America.The first reports on the chemistry of phthalides appeared at the end of the nineteenth century, in which they were identified as the odor constituents of the essential oil of celery (Apium graveolens) by Ciamician and Silber (1897). In the first half of the last century, phthalides were isolated from Cnidium officinale and Ligusticum acutilobum, species widely used in Asian traditional medicine, and from Levisticum officinale, a species used as food and condiment. Throughout the second part of the twentieth century, phthalides have been characterized from several plant families, namely Asteraceae, Leguminosae, Orchidaceae and Rutaceae, among others, but mainly from the Umbelliferae (syn Apiaceae) family, and the major contributors have been the following species used in traditional medicine: Ligusticum chuanxiong (Chinese name: Chuanxiong), Angelica sinensis (Chinese name: Danggui), Cnidium officinale (Japanese name: Senkyu), Angelica acutiloba (Japanese name: Toki), and Ligusticum porteri (Hispanic name: Oshá). Phthalides are also constituents of several genera of fungi, such as Penicillium, Alternaria and Pestalotiopsis, and some liverworts.Different chromatographic, spectrometric, and two-dimensional nuclear magnetic resonance (NMR) techniques have been used for the isolation and structural characterization of phthalides in extracts, and for assessing the quality of plant material containing this type of compound. Isotopic labeling has established the biosynthesis of phthalides via linkage of acetate units forming polyketide intermediates.Chemical transformations of monomeric phthalides have included oxidation, reduction, addition, elimination, and cycloaddition reactions, and treatments with Lewis acids of (Z)-ligustilide have afforded linear dimers. Some intramolecular condensations and differentiated cyclizations of the dimeric phthalides have been carried out, providing evidences for the particular chemical reactivity of these compounds.Several structural modifications of phthalides have been carried out subjecting them to microbial transformations by different species of bacteria, fungi and algae, and these included resolutions of racemic mixtures and oxidations, among others.The [π4s + π2s] and [π2s + π2s] cycloadditions of (Z)-ligustilide for the synthesis of dimeric phthalides have been reported, and different approaches involving cyclizations, Alder-Rickert reactions, Sharpless asymmetric hydroxylations, or Grignard additions have been used for the synthesis of monomeric phthalides. The use of phthalides as building blocks for divergent oriented synthesis has been proven.Many of the naturally occurring phthalides display different biological...

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Synthesis of certain n-butyltetra- and hexa-hydrophthalides

Cited by 8 publications

References 0 publications

Stereoisomeric Flavor Compounds. 79. Simultaneous Enantio- selective Analysis of 3-Butylphthalide and 3-Butylhexahydro- phthalide Stereoisomers in Celery, Celeriac, and Fennel

Stereoisomeric Flavor Compounds. 79. Simultaneous Enantio- selective Analysis of 3-Butylphthalide and 3-Butylhexahydro- phthalide Stereoisomers in Celery, Celeriac, and Fennel

Stereoisomeric flavor compounds LXXVII: 3‐Butylhexahydrophthalides: Simultaneous enantioselective analysis, structure elucidation, and sensorial properties of the stereoisomers

Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity

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