Molecular rearrangements of highly functionalized terpenes. an unique reactivity of bicyclic framework and polienic chain inhibition under superacidic treatment
Închide
Conţinutul numărului revistei
Articolul precedent
Articolul urmator
450 2
Ultima descărcare din IBN:
2017-03-28 16:56
SM ISO690:2012
GRINCO, Marina; KULCIŢKI, Veaceslav; VLAD, Pavel; BARBĂ, Alic; GORINCIOI, Elena; UNGUR, Nicon. 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.
EXPORT metadate:
Google Scholar
Crossref
CERIF
BibTeX
DataCite
Dublin Core
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: 10.19261/cjm.2013.08(2).12
Pag. 94-100

Grinco Marina, Kulciţki Veaceslav, Vlad Pavel, Barbă Alic, Gorincioi Elena, Ungur Nicon
 
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, superacid, isomerization.,

synthesis