Stereoselective Total Synthesis of Mucocin, an Antitumor Agent

The THP and THF rings which are regarded as the characteristic structural features of mucocin (1) were constructed by a SmI2-induced reductive cyclization of β-alkoxy acrylate and oxidative cyclization of a homoallyl alcohol, respectively. The key intermediates were synthesized through an efficient desymmetrization of a C2-symmetric tetraol.