Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B

Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B

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 an...

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Bibliographic Details
Main Authors: Khong, Duc Thinh, Judeh, Zaher M. A.
Other Authors: School of Chemical and Biomedical Engineering
Format: Article
Language:English
Published: 2020
Subjects:
Engineering::Bioengineering
Phenylpropanoid Glycosides
Phenylethanoid Glycosides
Online Access:https://hdl.handle.net/10356/138998
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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