cis-(-)-Menthyl phenylglycidates in the asymmetric synthesis of taxol side chain

ER M., Coskun N.

ARKIVOC, ss.153-160, 2009 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası:
  • Basım Tarihi: 2009
  • Doi Numarası: 10.3998/ark.5550190.0010.c13
  • Dergi Adı: ARKIVOC
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.153-160
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

The one-pot azidation and benzoylation of a mixture of cis (-)-menthyl phenylglycidates provide quantitatively the corresponding (2R,3S)-, and (2S,3R)-3-azido-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-1-oxo-3-phenylpropan-2-yl benzoate. Enantiopure (2R,3S)-3-azido-1((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)-1-oxo-3-phenylpropan-2-yl benzoate crystallize from MeOH at room temperature in high yields. The reduction of the latter with Zn-TMSCl produces (-)-menthyl 3-benzamido-3-phenyl-2-(trimethylsilyloxy) propanoate which upon simultanious desilylation and hydrolysis provide the taxol side chain N-benzoyl-(2R, 3S)-3-phenylisoserine.