Structure of α-ferulene a sesquiterpene having a (+)-aristolane skeleton

Carboni, S.; Settimo, A. Da; Malaguzzi, V.; Marsili, A.; Pacini, P.L.

doi:10.1016/s0040-4039(01)89251-0

Cited by 12 publications

(2 citation statements)

References 10 publications

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“…Consequently, structure (+)- 1 represents the relative and absolute configuration of natural allohedycaryol. This also means that natural (+)- 1 possesses the ent -configuration, which is remarkable because ent -sesquiterpenes are rarely found in higher plants . In addition, the possibility that (+)-hedycaryol ( 2 ) acts as a direct precursor of (+)- 1 can be ruled out because the ent -form of 2 has not been found in nature…”

Section: Resultsmentioning

confidence: 99%

Relative and Absolute Configuration of Allohedycaryol. Enantiospecific Total Synthesis of Its Enantiomer

et al. 1996

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The enantiomer of (+)-allohedycaryol, a germacrane alcohol isolated from giant fennel (Ferula communis L.), has been synthesized, thereby elucidating the relative and absolute stereochemistry of the natural product. The synthesis of (-)-allohedycaryol started from (+)-alpha-cyperone (5) which was available in relatively large quantities via alkylation of imine 7 derived from (+)-dihydrocarvone and (R)-(+)-1-phenylethylamine. In a number of steps 5 was converted into the mesylate 4with a regio- and stereoselective epoxidation as the key step. A Marshall fragmentation of 4 was used to prepare the trans,trans-cyclodeca-1,6-diene ring present in allohedycaryol. The conformation of synthetic (-)-allohedycaryol was elucidated via photochemical conversion into a bourbonane system. The synthesis of (-)-allohedycaryol also showed that natural (+)-allohedycaryol has the opposite absolute stereochemistry to that normally found in higher plants.

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Section: Resultsmentioning

confidence: 99%

Relative and Absolute Configuration of Allohedycaryol. Enantiospecific Total Synthesis of Its Enantiomer

et al. 1996

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“…The results of this study demonstrate that, despite the lack of morphological differences, a broad chemical diversity occurs within giant fennel, even in an insular environment where infraspecific diversity tends to be low. 19 Apart from the occurrence of the same phenylpropanes and siol esters, the only other chemical trait shared by the two chemotypes of F. communis growing in Sardinia is the accumulation of ent-sesquiterpenes (aristolanes 20 and germacranes, respectively), a rare feature in higher plants. Daucane esters are widespread in plants from the genus Ferula, 21 but the accumulation of sizable amounts of specific esters is rare.…”

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Oxygenated Sesquiterpenoids from a Nonpoisonous Sardinian Chemotype of Giant Fennel (Ferula communis)

et al. 2001

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The roots of the nonpoisonous chemotype of giant fennel (Ferula communis) from Sardinia afforded a novel cadinanetriol (1), whose structure was established by spectroscopic data and confirmed by synthesis from the E,E-Delta (1(10),5) germacradiene allohedycariol. A number of known compounds were also identified. Despite the lack of morphological differences, a broad chemical diversity exists within giant fennel, underlying the contrasting data on its poisonous properties.

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