| Abstract
| - The rapidly expanding field of combinatorial chemistryhas stimulated the development of new methodsand synthetic strategies for assembly of compound libraries. Wepropose four criteria that are desirable for syntheticroutes to such libraries: (1) the sequence involves a small number ofsteps; (2) no more than one variable is introducedin any step; (3) starting materials are readily obtained with a diverseselection of substituents, and (4) cyclic,nonoligomeric structures represent the most interesting targets.Guided by these criteria, we have explored anintramolecular version of the azomethine ylide cycloaddition reactionwhich utilizes readily available amino acids,aldehydes, and 2° amines as inputs. We prepared a number ofcycloadducts in solution to optimize conditions andexamine the scope of the process and to identify a synthetic strategythat would be amenable to solid-phase synthesisof these compounds. Transfer of the sequence to solid phase wasdemonstrated by the synthesis of a number ofrepresentative compounds, indicating that the chemistry is suitable forconstruction of a combinatorial library.
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