Synthesis and Structural Properties of Novel Tricyclic 15-membered Azalides

Synthesis and Structural Properties of Novel Tricyclic 15-membered Azalides

Starting from 3-decladinosyl-9a, 11-cyclic carbamates of 15 membered azalide, strained tricyclic aglycone derivatives were prepared. The bridging 5-membered hemiketal ring was obtained by intramolecular ketalization of intermediary 3-keto derivative, whereas 5-membered ether derivatives were obtaine...

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Veröffentlicht in:Croatica chemica acta 2009-12, Vol.82 (4), p.715
Hauptverfasser: Fajdetic, Andrea, Kobrehel, Gabrijela, Lazarevski, Gorjana, Marusic-Istuk, Zorica, Mutak, Stjepan
Format: Artikel
Sprache:eng
Schlagworte:
Antibiotics
Chemical synthesis
Spectrum analysis
Studies
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Zusammenfassung:Starting from 3-decladinosyl-9a, 11-cyclic carbamates of 15 membered azalide, strained tricyclic aglycone derivatives were prepared. The bridging 5-membered hemiketal ring was obtained by intramolecular ketalization of intermediary 3-keto derivative, whereas 5-membered ether derivatives were obtained by intramolecular Williamson-type displacement. In case of 12-O-alkyl derivatives complete diastereoslective formation of ethers was observed, while unsubstituted compound gave diastereomeric mixture. NMR analysis was used to confirm the structures of new tricyclic azalide compounds. [PUBLICATION ABSTRACT]
ISSN:0011-1643
1334-417X