Stereodivergent Synthesis of Enantioenriched Five- and Six-Membered Cyclic-1,3-diols and Applications Toward Library Synthesis

This work describes the development of methods to access synthetically useful chiral diols in enantiomerically pure form. First chapter describes the development of a stereodivergent approach for enantioenriched synthesis of 2-cyclopentene-1,3-diol that was later converted to 4-hydroxy-2-cyclopentenones (4-HCPs), which are highly privileged synthetic building blocks with numerous applications in natural product syntheses and pharmaceuticals. The present approach enables the gram scale synthesis of 4-HCPs with chemically diverse protecting groups, in a stereodivergent manner. In chapter 2, we describe the development of a unified strategy for the stereodivergent synthesis of enantioenriched 1,3-dihydroxy substituted six-membered carbo- and heterocyclic rings. The previously known approaches for accessing these compounds involve multiple synthetic steps and one or more enzymatic steps. We developed a purely synthetic approach to synthesize enantioenriched carbo- and heterocyclic six-membered 1,3-diols from a common, highly economical commercial available starting material. In Chapter 3, we described the development of a small-molecule library of stereochemically diverse compounds by integrating enantioenriched carbo- and heterocyclic 1,3-diols, and natural ?-amino acids.