Molecular rearrangements of highly functionalized terpenes. an unique reactivity of bicyclic framework and polienic chain inhibition under superacidic treatment
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GRINCO, Marina, KULCIŢKI, Veaceslav, VLAD, Pavel, BARBA, Alic, GORINCIOI, Elena, UNGUR, Nikon. Molecular rearrangements of highly functionalized terpenes. an unique reactivity of bicyclic framework and polienic chain inhibition under superacidic treatment. In: Chemistry Journal of Moldova, 2013, nr. 2(8), pp. 94-100. ISSN 1857-1727. DOI: https://doi.org/10.19261/cjm.2013.08(2).12
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Chemistry Journal of Moldova
Numărul 2(8) / 2013 / ISSN 1857-1727 /ISSNe 2345-1688

Molecular rearrangements of highly functionalized terpenes. an unique reactivity of bicyclic framework and polienic chain inhibition under superacidic treatment
DOI: https://doi.org/10.19261/cjm.2013.08(2).12

Pag. 94-100

Grinco Marina, Kulciţki Veaceslav, Vlad Pavel, Barba Alic, Gorincioi Elena, Ungur Nikon
 
Institute of Chemistry of the Academy of Sciences of Moldova
 
Disponibil în IBN: 26 februarie 2014


Rezumat

Synthesis of polyfunctional triterpene derivative [8(27),13E,17E,21E]-15-phenylsulfonyl-16-oxobicyclofarnesylfarnesol benzyl ether (8) from commercially available monoterpene geraniol and diterpene manool has been accomplished in 73% yield and its chemical transformation in superacid medium has been investigated. An unexpected rearrangement of 8 occurred, which involved methyl migration in the bicyclic fragment and total inhibition of the lateral polienic chain. A new bicyclic triterpene product [5(10),13E,17E,21E]-15-phenylsulfonyl- 16-oxo-30(10→9)-abeo-bicyclofarnesylfarnesol benzyl ether (9), with rearranged new carbon skeleton has been obtained. Its bicyclic moiety is analogous to this of a natural triterpene neopolypodatetraene.

Cuvinte-cheie
triterpenes, synthesis,

superacid,

isomerization.

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