The synthetic target of this project is cross-protected 1,11-diaza-6,16-ditosylamidacycloicosane (V).  Both halves of this macrocycle (V) are synthesized from a dinitrile (I).  The diamine (II) is synthesized via a reduction using borane�tetrahydrofuran.  Several carboxylic acid derivatives are being considered for cyclization with the diamine to form the diamide (IV), based on yield, stability, and preparation.  A similar borane reduction of the diamide yields the target macrocycle.  All synthesized compounds are characterized using IR, HR-MS and 1H-NMR spectroscopy. 

Progress towards a multi-gram scale synthesis of  1,11-diaza-6,16-ditosylamidacycloicosane

243rd National Meeting (2012)

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