Total Syntheses of (−)-Englerins A/B, (+)-Orientalols E/F, and (−)-Oxyphyllol

(−)-Englerin A was synthesized in 20 steps from the commercially available material (R)-(+)-limonene. In addition, (−)-englerin B, (+)-orientalol E/F and (−)-oxyphyllol were obtained from the intermediate in the route. The key steps include a hydroxyl-directing stereoselective and regioselective int...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2018-05, Vol.20 (9), p.2517-2521
Hauptverfasser: Liu, Pengcai, Cui, Yutao, Chen, Kang, Zhou, Xinyue, Pan, Wenyan, Ren, Jun, Wang, Zhongwen
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:(−)-Englerin A was synthesized in 20 steps from the commercially available material (R)-(+)-limonene. In addition, (−)-englerin B, (+)-orientalol E/F and (−)-oxyphyllol were obtained from the intermediate in the route. The key steps include a hydroxyl-directing stereoselective and regioselective intramolecular cyclopropanation and a multi-gram-scale stereoselective formal intramolecular [3 + 2] cross cycloaddition ([3 + 2]-IMCC) of a cyclopropane 1,1-diester with a carbonyl. A precursor of 7,10-diastereoisomer of englerins was also obtained.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00552