Strategies towards C-Glycosides

2 (9-Glycosides vs. C-Glycosides Comparisons of Physical Properties, Anomeric Effects, H-Bonding Abilities, Stabilities and Conformations 

4 Lewis Acid-Mediated Couplings with Olefins Arylation Reactions 

Reactions with Enol Ethers, Silylenol Ethers and Enamines 

Nitroalkylation Reactions Reactions with Allylic Ethers Wittig Reactions with Lactols 

Nucleophihc Additions to Sugar Lactones Followed by Lactol Reductions 7.2.9.1 Lewis Acid-Trialkylsilane Reductions 

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We selected the natural product thyrsiferol as an ideal target to test our ideas. Its total synthesis was envisioned to proceed as illustrated in the Scheme 28. The successful coupling between aldehyde 84 and vinyl iodide 82 via a Nozaki-Hiyama-Kishi (NHK) reaction [66] had been demonstrated previously [29]. We therefore sought to model our final steps after precedence presented by Forsyth for the union of these two fragments. The focus of our synthetic strategy centered around the stereoselective synthesis of the ABC framework (84) of thyrsiferol (1) as a scaffold to validate the scope of the Cp2TiCl reaction with epoxides toward the assembly of Q-C-glycosides and cyclic ethers. 

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