Novel synthesis of 2-Substituted 19-norvitamin D A-ring phosphine oxide from d-glucose as a building block

19-Norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from d-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2003-03, Vol.13 (5), p.809-812
Hauptverfasser:	Shimizu, Masato, Iwasaki, Yukiko, Shibamoto, Yoshinori, Sato, Miki, DeLuca, H.F, Yamada, Sachiko
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds, terpenoids, prostaglandins, steroids Calcitriol - analogs & derivatives Calcitriol - chemical synthesis Catalysis Chemistry Exact sciences and technology Glucose - chemistry Organic chemistry Oxides - chemical synthesis Oxides - chemistry Palladium - chemistry Phosphines - chemical synthesis Phosphines - chemistry Preparations and properties Stereoisomerism Steroids
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	19-Norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from d-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method. 19-Norvitamin D A-ring phosphine oxide was synthesized by a new sequence mode starting from d-glucose as a chiral template.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/S0960-894X(03)00005-2