Bai Xiaojie,Wu Siwei,Zhou Xiangdong.Stereoselective synthesis of cerebrosterol from porcine hyodeoxycholic acid[J].J Amry Med Univ (J Third Mil Med Univ),2016,38(11):1313-1318.
Bai Xiaojie,Wu Siwei,Zhou Xiangdong.Stereoselective synthesis of cerebrosterol from porcine hyodeoxycholic acid[J].J Amry Med Univ (J Third Mil Med Univ),2016,38(11):1313-1318.DOI:
Stereoselective synthesis of cerebrosterol from porcine hyodeoxycholic acid
Objective To establish a method to stereoselectively synthesize cerebrosterol. Methods The target molecule was synthesized through 9 steps including methyl esterification
reduction
Wittig reaction
Sharpless catalytic asymmetric dihydroxylation
etc.
with hyodeoxycholic acid as starting material
demosterol acetate as key intermediate
and Sharpless catalytic asymmetric dihydroxylation as key step. Results Cerebrosterol was synthesized with the total yield of 52% and stereoselectivity of 97% de
and it was identified by mass spectrometry (MS)
proton magnetic resonance spectroscopy (
1
HNMR)
carbon magnetic resonance spectroscopy (
13
CNMR)
infrared spectroscopy (IR)
elemental analysis
etc. Conclusion The synthesis of cerebrosterol is chara
cterized by high yield
high stereoselctivity
easy recrystallization and purification of each intermediate