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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description	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.
doi_str_mv	10.1002/anie.200902840
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subjects	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
title	Synthesis of (-)-Hygromycin A: Application of Mitsunobu Glycosylation and Tethered Aminohydroxylation
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