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All Journal The Journal of Pure and Applied Chemistry Research
Rurini Retnowati
Laboratory of Organic Chemistry, Department of Chemistry, Brawijaya University, Jl. Veteran No. 1 Malang, Indonesia 65145
Chemical Engineering, Chemistry & Bioengineering Chemistry Materials Science & Nanotechnology Medicine & Pharmacology

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Practical Preparation of (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate Yudhi Dwi Kurniawan; Duen-Ren Hou; Rurini Retnowati
The Journal of Pure and Applied Chemistry Research Vol 3, No 1 (2014)
Publisher : Chemistry Department, The University of Brawijaya

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (340.16 KB) | DOI: 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%.
Co-Authors Duen-Ren Hou Yudhi Dwi Kurniawan