Affordable Access

deepdyve-link
Publisher Website

Stereospecific synthesis and rearrangement of 22S-23-acetylsapogenins.

Authors
  • Lu, Yi-Hong1
  • Xie, Yang2
  • Hu, Pei3
  • Sun, Zhao-Lin3
  • Li, Zhi-Xiong4
  • Huang, Cheng-Gang5
  • 1 Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. , (China)
  • 2 Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310027, China. , (China)
  • 3 Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China. , (China)
  • 4 Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China. Electronic address: [email protected] , (China)
  • 5 Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. Electronic address: [email protected] , (China)
Type
Published Article
Journal
Steroids
Publication Date
Aug 01, 2020
Volume
160
Pages
108655–108655
Identifiers
DOI: 10.1016/j.steroids.2020.108655
PMID: 32439406
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The BF3·Et2O-catalysed acetolysis of steroid sapogenins diosgenin, sarsasapogenin and tigogenin in dichloromethane as the solvent instead of acetic anhydride afforded (20S)- and (20R)-22,26-epoxycholestanes (compounds 1 and 2). 22S-23-Acetylsapogenins (compounds 4) were synthesized stereospecifically from 20R-22,26-epoxycholestanes (compounds 2) in good yield. The rearrangement of 22S-23-acetylsapogenins (compounds 4) afforded novel disubstituted dihydropyran furostanol frameworks. Exhaustive NMR characterization of the obtained compounds is provided. Additionally, the structures of the critical compounds (6a and 7a) were unequivocallyconfirmed by single crystal X-ray diffraction studies. Copyright © 2020 Elsevier Inc. All rights reserved.

Report this publication

Statistics

Seen <100 times