Part I Cascade reaction : Mukaiyama-Aldol-Prins (MAP) and Mukaiyama-Aldol-Ene (MAE) Part II Synthetic studies towards the total synthesis of cytochalasans
Date of Issue2010
School of Physical and Mathematical Sciences
Mukaiyama-Aldol and Prins reactions have been testified as highly efficient methods in C-C bond formation since they were discovered several decades ago. Since both reactions gave the same common intermediate, called oxocarbonium II, we intend to combine the two reactions into a domino process, which means the formation of multiple C-C bonds and stereogenic centers in one pot without isolation of any intermediates. We envisage that the domino reactions involving the Mukaiyama-Aldol reaction of silyl enol ether III and acetal I treated with Lewis acid (e.g. TiBr4) will produce an oxonium intermediate IV which upon trapping by an alkene functionality in an intramolecular Prins cyclization fashion will generate the cyclopentyl ring system VI (path a).
Nanyang Technological University