Date of Completion

8-22-2014

Embargo Period

8-22-2015

Keywords

macrolide, synthesis, structure, natural product-like, antibiotic, carbohydrate

Major Advisor

Dr. Mark W. Peczuh

Associate Advisor

Dr. Edward J. Neth

Associate Advisor

Dr. Dennis L. Wright

Field of Study

Chemistry

Degree

Doctor of Philosophy

Open Access

Campus Access

Abstract

Natural product-like molecules containing a macrocycle are attractive synthetic targets due to their novel molecular architectures. Additionally, they often present biological activity. Previous efforts from our group delivered carbohydrate-fused [13]-macrodilactones. The macrodilactones are built off C4 and C6 position of the carbohydrate. We also prepared macrolactones that are fused through the C1 and C5 positions of a pyranose ring. The connectivity to the carbohydrate affords a bicyclic system featuring a one atom bridge between ring systems. The novel macrolactones have been produced via a concise synthetic sequence that includes acylation of a 1-allyl glycoside followed by ring closing metathesis (RCM). [12], [13] and [14] member lactones which contain an alkene have been produced. Structural investigations of the new macrocycles including crystallographic data have been obtained. Presentation of mild antibiotic activity from the [12] membered macrocycles prompted diversification at C4 of the pyranose system to develop a biological profile of the new targets.

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