Evaluation of the Biosynthetic Proposal for the Synthesis of Marineosins A and B

Evaluation of the Biosynthetic Proposal for the Synthesis of Marineosins A and B

The first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1−C25 Diels−Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomi...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2010-03, Vol.12 (5), p.1048-1051
Hauptverfasser: Aldrich, Leslie N, Dawson, Eric S, Lindsley, Craig W
Format: Artikel
Sprache:eng
Schlagworte:
Biomimetics
Electron Transport
Models, Molecular
Molecular Conformation
Pyrroles - chemical synthesis
Pyrroles - metabolism
Spiro Compounds - chemical synthesis
Spiro Compounds - metabolism
Streptomyces - metabolism
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The first synthetic efforts toward marineosins A and B, novel spiroaminals from a Streptomyces actinomycete, are described by evaluation of the proposed biosynthesis. The hypothesized biosynthetic C1−C25 Diels−Alder substrate was prepared in 8 steps in 5.1% overall yield; however, the proposed biomimetic inverse-electron-demand hetero-Diels−Alder reaction failed to deliver the marineosin core. Molecular mechanics supports this observation.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100034p