Croatica Chemica Acta, Vol. 82 No. 4, 2009.
Original scientific paper
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
Abstract
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.
Keywords
Macrolides; azalides; synthesis; tricyclic structures; NMR spectroscopy
Hrčak ID:
45437
URI
Publication date:
20.12.2009.
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