Stereoselective Reduction of Bicyclic Ketals. A New, Enantioselective Synthesis of Isolaurepinnacin and Lauthisan Skeletons

Article abstract of DOI:10.1021/jo00282a037

A general synthetic strategy for constructing seven- and eight-membered cyclic ether derivatives is described.The important feature of this work is a highly stereoselective reduction of bicyclic ketals, i.e., cis-selective reduction with triethylsilane/TiCl4 and trans-selective reduction with diisobutylaluminum hydride (DIBAL).The procedure completed a new and efficient synthesis of isolaurepinnacin and lauthisan skeletons in optically active forms.