The Total Synthesis of (−)-SNF4435 C and (+)-SNF4435 D

The Total Synthesis of (−)-SNF4435 C and (+)-SNF4435 D

The size and positioning of substituents on a tetraene, along with the Woodward−Hoffmann rules, control the relative stereochemistry at the four adjacent chiral centers that are generated in the 8π/6π electrocyclization cascade. A biomimetic synthesis of (−)-SNF4435 C and (+)-SNF4435 D exploits thes...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2004-12, Vol.126 (49), p.15968-15969
Hauptverfasser: Parker, Kathlyn A, Lim, Yeon-Hee
Format: Artikel
Sprache:eng
Schlagworte:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Chemistry
Exact sciences and technology
Immunosuppressive Agents - chemical synthesis
Medical sciences
Miscellaneous. Antibiotics with multiple activities
Nitro Compounds - chemical synthesis
Organic chemistry
Pharmacology. Drug treatments
Preparations and properties
Pyrones - chemical synthesis
Stereoisomerism
Streptomyces - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The size and positioning of substituents on a tetraene, along with the Woodward−Hoffmann rules, control the relative stereochemistry at the four adjacent chiral centers that are generated in the 8π/6π electrocyclization cascade. A biomimetic synthesis of (−)-SNF4435 C and (+)-SNF4435 D exploits these steric effects and allows confirmation of the predicted absolute stereochemistry of the natural products.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja044733l