- One-step synthesis of furan rings from α-isopropylidene ketones mediated by iodine/DMSO: An approach to potent bioactive terpenes
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The system I2/dimethyl sulfoxide mediates the one-step transformation of α-isopropylidene ketones into furan rings following a biomimetic approach. This methodology has been used for the synthesis of terpene furans such as mintfurane, curzerene, atractylon, and isoatractylon, all of them possessing interesting biological activities. The synthesis of linderazulene directly from 4,5-epoxygermacrone via a cascade reaction shows the potential of this protocol. Additionally, this compound proved to show significant ixodicidal activity.
- Salihila, Jonida,Silva, Lúcia,Pérez Del Pulgar, Helena,Quílez Molina, Ana,González-Coloma, Azucena,Olmeda, A. Sonia,Quílez Del Moral, José F.,Barrero, Alejandro F.
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p. 6886 - 6894
(2019/06/14)
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- Dimerization of butenolide structures. A biomimetic approach to the dimeric sesquiterpene lactones (±)-biatractylolide and (±)- biepiasterolide
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The biomimetic synthesis of the bisesquiterpene lactones (±)-biatractylolide 1 and (±)-biepiasterolide 2 via dimerization of the captodative stabilized radical 8 is reported. Atractylon 7 has also been shown to be a possible intermediate during the biosynthesis of biatractylolide 1, biepiasterolide 2, atractylolide 3, and hydroxyatractylolide 4.
- Bagal, Sharanjeet K.,Adlington, Robert M.,Baldwin, Jack E.,Marquez, Rodolfo
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p. 9100 - 9108
(2007/10/03)
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- Sesquiterpene Metabolites of the Antarctic Gorgonian Dasystenella acanthina
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The ethereal extract of the Antarctic gorgonian Dasystenella acanthina was found to contain three main nonpolar and relatively transient sesquiterpene metabolites (1-3), which were isolated and submitted to spectral analysis. Two of them were identified as the previously reported compounds trans-β-farnesene (1) and isofuranodiene (3), whereas the third metabolite, the furanoeudesmane 2, was unknown. The structure elucidation of this new sesquiterpene was solved mainly on the basis of its spectral properties and correlation with known compounds.
- Gavagnin, Margherita,Mollo, Ernesto,Castelluccio, Francesco,Crispino, Antonio,Cimino, Guido
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p. 1517 - 1519
(2007/10/03)
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- TOTAL SYNTHESIS OF (+/-)-ATRACTYLON AND (+/-)-LINDESTRENE
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The total synthesis of the eudesmane furanosesquiterpenes (+/-)-atractylon (1) and (+/-)-lindestrene (2) is described.Both 1 and 2 were synthesized via the methyl xanthate intermediate (10).
- Honan, Matthew C.
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p. 6393 - 6396
(2007/10/02)
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- Structures of Novel Sesquiterpene Alcohols from Chloranthus japonicus (Chloranthaceae)
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Tree novel sesquiterpene alcohols, shizuka-acoradienol (2), shizukafuranol (3) and shizukolidol (4), were isolated from Chloranthus japonicus Sieb. (Japanese name: Hitori-shizuka, Chloranthaceae).Their structures were elucidated on the basis of their physicochemical properties and some chemical reactions.Furanodienone (5), scopoletin (6a) and isoscopoletin (6b) were also isolated from this plant.
- Kawabata, Jun,Fukushi, Yukiharu,Tahara, Satoshi,Mizutani, Junya
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p. 713 - 718
(2007/10/02)
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- An Annelation Approach to the Synthesis of Eudesmane and Elemane Sesquiterpene Lactones. Total Synthesis of dl-Dihydrocallitrisin, dl-7,8-Epialantolactone, dl-7,8-Epiisoalantolactone, and dl-Atractylon
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An annelation approach to the synthesis of eudesmane sesquiterpenes is described.The 1,6-annelation reagent α-carbomethoxy-β-methyl-γ-methylidene-Δα,β-butenolide (1) is used to construct the linear tricyclic lactone 2,5,6,7,8,8a,9,9aβ-octahydro-8aβ-methyl-2-oxonaphthofuran-3-carboxylic acid methyl ester (2).The conversion of 2 to dl-dihydrocallitrisin (3), dl-7,8-epialantolactone (4), dl-7,8-epiisoalantolactone (5), and dl-atractylon (6) is detailed.Studies directed toward synthesis of the elemane sesquiterpene lactones vernomenin and vernolepin also are presented.
- Schultz, Arthur G.,Godfrey, Jollie D.
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p. 2414 - 2428
(2007/10/02)
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