Practical Preparation of (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate

Authors

  • Yudhi Dwi Kurniawan University of Brawijaya
  • Duen-Ren Hou Department of Chemistry, National Central University, 300 Jhong-Da Road, Jhong-Li, Taoyuan, Taiwan
  • Rurini Retnowati Laboratory of Organic Chemistry, Department of Chemistry, Brawijaya University, Jl. Veteran No. 1 Malang, Indonesia 65145

DOI:

https://doi.org/10.21776/ub.jpacr.2014.003.01.164

Keywords:

acrylate, olefin, cross-metathesis, Grubbs’ catalyst, copper iodide

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%.

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References

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Published

2013-12-09

Issue

Vol. 3 No. 1 (2014)

Section

Articles

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How to Cite

Practical Preparation of (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate. (2013). The Journal of Pure and Applied Chemistry Research, 3(1), 13-18. https://doi.org/10.21776/ub.jpacr.2014.003.01.164