Practical Preparation of (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate
Yudhi Dwi Kurniawan, Duen-Ren Hou, Rurini Retnowati
J. Pure App. Chem. Res. Vol 3, No 1 (2014), pp. 13-18
Submitted: September 24, 2013     Accepted: October 19, 2013     Published: December 09, 2013
DOI: http://dx.doi.org/10.21776/ub.jpacr.2014.003.01.164

Abstract



This study is aimed to improve the preparation of uselful synthetic block (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate (1). This intermediate was used in the synthesis of (+)-Cladospolide D. The strategy developed by Voigtritter et al. was adopted to exploit the acceleration effect of copper (I) iodide. This compound was prepared from D-mannitol-derived dienediol (2) coupled with methyl acrylate through olefin cross-metathesis reaction in various conditions. It was found that performing the reaction in the presence of 3 mol% of CuI in refluxing diethyl ether gave the product up to 75% of yield with lower catalyst loading, i.e.: 2 mol%.

Keywords : acrylate; olefin; cross-metathesis; Grubbs’ catalyst; copper iodide
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