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Final‐Stage Site‐Selective Acylation for the Total Syntheses of Multifidosides A–C
Author(s) -
Ueda Yoshihiro,
Furuta Takumi,
Kawabata Takeo
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504729
Subject(s) - acylation , total synthesis , chemistry , single stage , protecting group , functional group , combinatorial chemistry , catalysis , organic chemistry , polymer , alkyl , engineering , aerospace engineering
The first total syntheses of multifidosides A–C have been achieved. The synthetic strategy is characterized by catalytic site‐selective acylation of unprotected glycoside precursors in the final stage of the synthesis. High functional‐group tolerance of the site‐selective acylation, promoted by an organocatalyst, enabled the conventionally difficult molecular transformation in a predictable and reliable manner. An advantage of this strategy is to avoid the risks of undesired side reactions during the removal of the protecting groups at the final stage of the total synthesis.