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Application of Interrupted Pummerer Reaction Mediated (IPRm) Glycosylation in Natural Product Synthesis
Author(s) -
Zhao Xiang,
Zeng Jing,
Meng Lingkui,
Wan Qian
Publication year - 2020
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201900097
Subject(s) - glycosylation , glycoconjugate , glycosidic bond , natural product , glycosyl , chemistry , pummerer rearrangement , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , enzyme , acetic anhydride
Although numerous glycosylation methods have been developed for the construction of glycosidic bonds, the pace of discovering rapid assembly strategies to access complex glycosidic linkages never stops. Over the last several years, we have introduced interrupted Pummerer reaction into carbohydrate chemistry and developed two pairs of latent/active glycosyl donors, OPTB/OPSB and SPTB/SPSB glycosides. After thorough investigation of the reaction mechanism and establishment of the substrate scopes, the extension of these novel glycosylation methods to synthesize naturally occurring biological active glycoconjugates was further illustrated. In this account, the development and especially the application of IPRm glycosylation in the synthesis of phenylethanoids and resin glycosides were introduced.