First total synthesis of tuberonic acid

作者：Nonaka Hisato; Wang Yong Gang; Kobayashi Yuichi^*

来源：Tetrahedron Letters, 2007, 48(10): 1745-1748.

DOI：10.1016/j.tetlet.2007.01.035

• tuberonic acid
• total synthesis
• stereoselective
• monoacetate of 4-cyclopentene-1,3-diol

A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2=CHMgBr, LiCl and a CuCN catalyst to produce the S(N)2-type product, from which the full carbon skeleton of tuberonic acid was constructed through Mitsunobu inversion, Claisen rearrangement, and Wittig reaction. At the last stage, the THP protective group was removed with MgBr2 in Et2O. The diastereomeric ratio of tuberonic acid and the trans isomer was 92:8 by H-1 NMR spectroscopy.

• 出版日期2007-3-5