Candida cylindracea

• 英文名称: Candida cylindracea

反应信息

• 作为试剂：
  描述：

  乙酸乙烯酯 、 (1S)-(-)-莰烷酰氯 、 meso-1,1'-methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl] 在 Candida cylindracea 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以34 mg的产率得到(1R,3R,5R)-1-{[(1S,3S,5S)-3-(acetyloxy)-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl}-8-oxabicyclo[3.2.1]oct-6-en-3-yl 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Enzymatic desymmetrization of 1,1′-methylenedi[(1R,1′S,3R,3′S,5S,5′R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-ene-1-yl]: novel precursors of long chain polyketides

  摘要：

  meso-1,1'-Methylenedi[(1R,1'S,3R,3'S,5S,5'R)-3-hydroxy-S-oxabicyclo[3.2.1]oct-6-ene-1-yl] 14 obtained through the [4+3]-cycloaddition of 2,T-methylenedifuran to oxyallyl cation, followed by reduction, has been desymmetrized by means of a lipase catalyzed transesterification to afford (1 S,3S,5S)-1-{[(1 R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2. 1]oct-6-en-yl]methyl)-8-oxabicyclo[3.2.1]loct-6-en-3-yl acetate (-)-15 (89% ee). This compound was transformed into aromatic ester derivatives for establishing the absolute configuration. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.038