Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C-H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin

Ohira Susumu, Kuboki Atsuhito, Takimoto Yoshimi, Matsuda Kyosuke, Itasaki Saori, Urushibata Yuki, Takano Yoshiyuki, Nakamura Yuuki

The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C-H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known synthetic intermediate for (+)-trehazolin was synthesized from D-diethyl tartrate. In addition, a short route to the intermediate from a D-mannitol derivative was described.                                                                                                                                                               
            

Tetrahedron Letters

Elesevier

60

39

151085