Abstract
An efficient and practical three-step synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B in >62% overall yield is disclosed. The key step involves the chemoselective and regio selective direct O -4 cinnamoylation of unprotected 2-phenylethyl-β- d -glucosides with cinnamic anhydrides using a chiral 4-pyrrolidinopyridine organocatalyst. This approach serves as a model for the short synthesis of phenylpropanoid glycosides acylated at O -4 without protection/deprotection steps.
| Original language | English |
|---|---|
| Pages (from-to) | 1079-1083 |
| Number of pages | 5 |
| Journal | Synlett |
| Volume | 29 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - May 14 2018 |
| Externally published | Yes |
Bibliographical note
Publisher Copyright:© Georg Thieme Verlag Stuttgart, New York.
ASJC Scopus Subject Areas
- Organic Chemistry
Keywords
- C -symmetric chiral 4-pyrrolidino pyridine
- calceolarioside A
- chemoselective
- phenylethanoid glycosides
- phenylpropanoid glycosides
- regioselective acylation
- syringalide B