Unexpected Diels–Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin

Unexpected Diels–Alder/Carbonyl-ene Cascade toward the Biomimetic Synthesis of Chloropupukeananin

The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels–Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2013-04, Vol.15 (7), p.1748-1751
Hauptverfasser: Suzuki, Takahiro, Miyajima, Yuria, Suzuki, Kaname, Iwakiri, Kanako, Koshimizu, Masaki, Hirai, Go, Sodeoka, Mikiko, Kobayashi, Susumu
Format: Artikel
Sprache:eng
Schlagworte:
Biomimetics
Models, Molecular
Molecular Structure
Salicylates - chemistry
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Stereoisomerism
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels–Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400549q