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Stereoselective Total Synthesis of Mucocin, an Antitumor Agent

2002; Wiley; Volume: 41; Issue: 24 Linguagem: Inglês

10.1002/anie.200290038

1521-3773

Shunya Takahashi, Akemi Kubota, Tadashi Nakata,

Chemical synthesis and alkaloids

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.