Synthesis of (−)-Agelastatin A by [3.3] Sigmatropic Rearrangement of Allyl Cyanate

Synthesis of (−)-Agelastatin A by [3.3] Sigmatropic Rearrangement of Allyl Cyanate

Total synthesis of (−)-agelastatin A has been achieved starting from l-arabitol. The highlights in our synthesis include the preparation of vicinal diamine moiety by [3.3] sigmatropic rearrangement of allyl cyanate and construction of central ring-C with ring-closing metathesis.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2007-08, Vol.9 (16), p.2989-2992
Hauptverfasser: Ichikawa, Yoshiyasu, Yamaoka, Tomonori, Nakano, Keiji, Kotsuki, Hiyoshizo
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Alkaloids - chemistry
Allyl Compounds - chemistry
Catalysis
Cyanates - chemistry
Molecular Structure
Oxazolidinones - chemical synthesis
Oxazolidinones - chemistry
Stereoisomerism
Sugar Alcohols - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Total synthesis of (−)-agelastatin A has been achieved starting from l-arabitol. The highlights in our synthesis include the preparation of vicinal diamine moiety by [3.3] sigmatropic rearrangement of allyl cyanate and construction of central ring-C with ring-closing metathesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0709735