Natural product-like molecules containing a macrocycle are attractive synthetic targets due to their novel molecular architectures. Additionally, they often present biological activiity. Previous efforts from our group delivered carbohydrate-fused [11.4.0] macro-dilactones. We also prepared macrolactones that are fused through the C1 and C5 positions of a pyranose ring. The connectivity to the carbohydrate affords a [n.3.1] bicyclic system. 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 has prompted diversification at C4 of the [9.3.1] pyranose system to develop a biological profile of the new targets.

Synthesis and biological evaluation of natural product-like macrocycles containing integral carbohydrate moieties

244th National Meeting (2012)

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