Von Cycloolefinen zu linearenC2-symmetrischen 1,4-Diamino-2,3-diol-Bausteinen – Peptidmimetica, Biokatalyse und Pinakol-Kupplung von α-Aminoaldehyden

Trifluoromethanesulfonic acid anhydride (triflic acid anhydride) transforms the bicyclic thiazolidinlactam 1 a into the crystalline elimination product 2, in which all four secondary hydroxyl groups of 1 a are differently functionalized. Compound 2 can then add nucleophiles with high chemo- and stereoselectivity. Altogether, the four secondary hydroxyl groups of D-glucuronic acid are selectively transformed without the need for any O-protecting groups. Minimizing the number of O-protecting groups is a prerequisite for the use of sugar scaffolds in molecular libraries. The hapalosin analogues 15, 16, 19, and 22 outline the strategy towards O-diversified glucose derivatives.

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Regioselective Conversion of the Secondary Hydroxyl Groups of D‐Glucuronic Acid without the Requirement of O‐Protecting Groups

Ágoston

Geyer

2005

Chemistry A European J

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Von Cycloolefinen zu linearenC2-symmetrischen 1,4-Diamino-2,3-diol-Bausteinen – Peptidmimetica, Biokatalyse und Pinakol-Kupplung von α-Aminoaldehyden

Cited by 1 publication

References 27 publications

Regioselective Conversion of the Secondary Hydroxyl Groups of D‐Glucuronic Acid without the Requirement of O‐Protecting Groups

Regioselective Conversion of the Secondary Hydroxyl Groups of D‐Glucuronic Acid without the Requirement of O‐Protecting Groups

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