Adenine activation with bromine

The total synthesis of quantamycin [61], necessitated the development of methodology to create a somewhat strained tra j-peihydrofuropyran structure with the required appendages. The adenine moiety was attached by a unique method whereby a bicyclic thioglycoside was treated sequentially with N-benzoyl adenine and bromine [62]. Quantamycin was found to have approximately 8-10% inhibition of binding of lincomycin or erythromycin at the same concentration to ribosomes from Streptomyces. However, no in vitro antibacterial activity was found, which may be an intrinsic problem, or a pharmacodynamic effect due to improper partitioning. 

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