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Synthesis and Structural Properties of Novel Tricyclic 15-membered Azalides

Andrea Fajdetić ; GlaxoSmithKline Research Centre Zagreb Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia
Gabrijela Kobrehel ; GlaxoSmithKline Research Centre Zagreb Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia
Gorjana Lazarevski ; GlaxoSmithKline Research Centre Zagreb Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia
Zorica Marušić-Ištuk ; GlaxoSmithKline Research Centre Zagreb Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia
Stjepan Mutak ; GlaxoSmithKline Research Centre Zagreb Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia

Sažetak

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.

Ključne riječi

Macrolides; azalides; synthesis; tricyclic structures; NMR spectroscopy

Hrčak ID:

45437

URI

https://hrcak.srce.hr/45437

Datum izdavanja:

20.12.2009.

Posjeta: 1.722 *