Synthesis of a Polycyclic Halichondrin C1–C14 Fragment via Intermolecular Oxy-Michael/Trans-Ketalization

Synthesis of a Polycyclic Halichondrin C1–C14 Fragment via Intermolecular Oxy-Michael/Trans-Ketalization

Syntheses of a crystalline polycyclic halichondrin C1–C14 building block starting from a d-gulono-1,4-lactone-derived intermediate in the current Halaven manufacturing process are described. Key features of the syntheses include an acid-catalyzed tandem intermolecular oxy-Michael/intramolecular tran...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2019-04, Vol.84 (8), p.4898-4903
Hauptverfasser: Kim, Dae-Shik, Fang, Francis G, Choi, Hyeong-wook, Fang, Hui
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Syntheses of a crystalline polycyclic halichondrin C1–C14 building block starting from a d-gulono-1,4-lactone-derived intermediate in the current Halaven manufacturing process are described. Key features of the syntheses include an acid-catalyzed tandem intermolecular oxy-Michael/intramolecular trans-ketalization reaction and stereoselective Kishi reductions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02404