We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Improved synthesis of gastrodin, a bioactive component of a traditional Chinese medicine.
- Authors
YU-WEN LI; CUI-LI MA
- Abstract
Highly practical, four-step synthesis of gastrodin was developed using penta-O-acetyl-β-D-glucopyranose and p-cresol as glycosyl donor and glycosyl acceptor, respectively, in 58.1 % overall yield. As the initial step, the penta-O-acetyl-β-D-glucopyranose was treated with p-cresol in the presence of BF3·Et2O as catalyst to generate 4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 76.3 % yield. Further, this product was subjected to radical bromination with N-bromosuccinimide (NBS) to provide 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 91 % yield. Subsequently, reaction of 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside with a solution of acetone and saturated aqueous sodium bicarbonate led to 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 93 % yield. Finally, global deprotection of 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside under Zemplen conditions furnished gastrodin in 90 % yield. Compared to the previously reported methods, this protocol has the advantages of operational simplicity, chromatography-free separation, high overall yield, inexpensive and common reagents as well as less waste pollutants, rendering it an alternative suitable for industrial production.
- Subjects
PHENOL synthesis; BIOACTIVE compounds; CHINESE medicine; BROMOSUCCINIMIDE; INDUSTRIAL productivity; BROMINATION
- Publication
Journal of the Serbian Chemical Society, 2014, Vol 79, Issue 10, p1205
- ISSN
0352-5139
- Publication type
Article
- DOI
10.2298/JSC131011026L