Title of article
First total synthesis of tuberonic acid
Author/Authors
Nonaka، نويسنده , , Hisato and Wang، نويسنده , , Yong-Gang and Kobayashi، نويسنده , , Yuichi، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2007
Pages
4
From page
1745
To page
1748
Abstract
A vinyl group as an acetic acid side chain was attached to the optically active monoacetate of 4-cyclopentene-1,3-diol with CH2CHMgBr, LiCl, and a CuCN catalyst to produce the SN2-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 1H NMR spectroscopy.
Keywords
Tuberonic acid , total synthesis , Monoacetate of 4-cyclopentene-1 , 3-diol , stereoselective
Journal title
Tetrahedron Letters
Serial Year
2007
Journal title
Tetrahedron Letters
Record number
1854392
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