Amino acids are among the most functionalized, easily manipulated, and inexpensive members of nature's chiral pool. As such, we have utilized these readily available templates to design and create chiral iodo-N,O-acetonide aminal platforms that facilitate complex molecule synthesis. These novel platforms, efficiently constructed via a multicomponent reaction developed in our laboratories, contain two contiguous nonepimerizable chiral centers which can be tuned depending upon the absolute configuration of the template amino acid.  Herein, we disclose synthetic methods whereby these broadly-applicable platforms can be used to construct a wide variety of complex biologically-relevant architectures including the natural product (-)-galantinic acid, and �smart� therapeutics designed to simultaneously target, detect, and treat disease.

Exploring the utility of novel amino acid-derived chirons: Toward the synthesis of (-)-galantinic acid and "smart" therapeutics

245th National Meeting (2013)

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