Synthesis of (-)-Hygromycin A: Application of Mitsunobu Glycosylation and Tethered Aminohydroxylation

Synthesis of (-)-Hygromycin A: Application of Mitsunobu Glycosylation and Tethered Aminohydroxylation

Key points in the synthesis of (−)‐hygromycin A are the tethered aminohydroxylation reaction used to prepare the aminocyclitol unit and the choice of a bulky protecting group on the sugar unit to facilitate selective Mitsunobu glycosylation and also bestow kinetic stability upon an otherwise vulnera...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (35), p.6507-6510
Hauptverfasser: Donohoe, Timothy J, Flores, Aida, Bataille, Carole J.R, Churruca, Fátima
Format: Artikel
Sprache:eng
Schlagworte:
aminohydroxylation
Anti-Bacterial Agents - chemical synthesis
Cinnamates - chemical synthesis
Glycosylation
Hygromycin B - analogs & derivatives
Hygromycin B - chemical synthesis
Mitsunobu glycosylation
natural products
Streptomyces - chemistry
total synthesis
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Zusammenfassung:Key points in the synthesis of (−)‐hygromycin A are the tethered aminohydroxylation reaction used to prepare the aminocyclitol unit and the choice of a bulky protecting group on the sugar unit to facilitate selective Mitsunobu glycosylation and also bestow kinetic stability upon an otherwise vulnerable proton.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200902840