Diastereoselective aldol reactions and applications to various natural product frameworks

Research in our lab has shown that lithium enolate additions to chloroaldehydes occurs selectively to yield predominantly anti-ketochlorohydrins (1). These enantioenriched building blocks can be further functionalized to provide scaffolds for various natural products; this includes reduction and cyclization to yield substituted tetrahydrofuranols (2) or radical dehalogenation to produce asymmetric hydroxyketone moieties (3). Research presented will include enantioselective synthesis of natural products Laurefurenynes A and B (4) and Solistatin (5) using this recently developed methodology.