Naslov
Regioselective and Stereospecific Methoxylation of Aucubin: An access to Novel Antibacterial Iridoid Derivatives

Autori
El Mourabet, M. ; Lecsö, M. ; Salle De Chou, Y. ; Markovic, D. ; Litaudon, M. ; Butel, M.-J. ; Deguin B.

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of Abstracts / - Marseille, 2013, 445-445

Skup
18th European Symposium on Organic Chemistry 2013,

Mjesto i datum
Marseille, Francuska, 7-12 Jully

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Aucubin, Aucuba japonica Thumb, Antibiotic, Iridoid, chiral pool syntheses

Sažetak
The use of natural iridoid glycosides as starting materials for the synthesis of biologically active compounds received considerable attention in the last decade. Aucubin rapidly appeared particularly suitable for the synthetic use since it is readily available in large amounts from the fresh aerial parts of a Aucuba japonica Thumb. Indeed aucubin in readily indeed aucubin analogues monoterpene basic core permitted the chiral pool syntheses of insect antifeedance, carboxylic nucleoside analogs, amiinocyclopentitol glycloside inhibitors and numerous prostagladins. More recent synthetic applications took advantage of both the aglycone and glucose moieties present in the natural iridoid as illustrated by the synthesis of homochiral rigid amino acid glucosides, citotoxic cyclopentanone glucosides and polyaminoiridoids whose structure may be related to the aminoside antibiotics. In this context, the development of techniques permitting successive or simultaneous modification of the aglycone and the glucose unit appeared particularly desirable, in order to access to the enlarged variety of synthetic derivatives of aucubin. When performed on the aucubin-derived substrates, diverse selective protection gave an access to the library of 17 aucubin derivatives. The antibacterial evaluation of these series led to the identification of a potential novel antibiotic compounds. We are knowledge financial support from the ANR (ANR-09-CP2D-09).

Izvorni jezik
Engleski

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