Studies on the Total Synthesis of Formamicin:  Synthesis of the C(1)−C(11) Fragment

Studies on the Total Synthesis of Formamicin:  Synthesis of the C(1)−C(11) Fragment

An efficient and highly concise synthesis of 6, corresponding to the C(1)−C(11) fragment of formamicin (1), has been accomplished by a route utilizing a diastereoselective lactate aldol reaction to set the C(6) tertiary ether and the TES−OTf mediated transketalization of the C(6) tertiary methoxymet...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2001-02, Vol.3 (3), p.453-456
Hauptverfasser: Powell, Noel A, Roush, William R
Format: Artikel
Sprache:eng
Schlagworte:
Actinomycetales - chemistry
Anti-Bacterial Agents - chemical synthesis
Antifungal Agents - chemical synthesis
Macrolides
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:An efficient and highly concise synthesis of 6, corresponding to the C(1)−C(11) fragment of formamicin (1), has been accomplished by a route utilizing a diastereoselective lactate aldol reaction to set the C(6) tertiary ether and the TES−OTf mediated transketalization of the C(6) tertiary methoxymethyl ether and the C(25) PMB ether to set the seven-membered methylene acetal unit (see 37 → 38).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0069610