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Construction of a Follow-Up Library and Binding Studies. The observation that the majority of potent binding compounds possessed basic nitrogen prompted us to consider the construction of unique analogues containing alternative basic nitrogen heterocycles.the ideal method would furnish the heterocyclic products diastereoselectively with a minimum of manipulations and allow for independent functionalization at both the left- and righthand hemispheres on the core scaffold. During the scale-up of Stemona scaffolds for library synthesis, we noted that the tandem Diels¨CAlder/Schmidt reaction could be halted at the Diels¨CAlder stage and the azido diketone product isolated by judicious choice of Lewis acid and by limiting the number of equivalents added. |
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