First total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside, an ophiopogonis saponin from the tuber of Liriope muscari (Decne.)

• Published in: Tetrahedron letters Vol. 39; no. 5; pp. 415 - 418
• Main Authors: Liu, Meizheng, Yu, Biao, Hui, Yongzheng
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 1998
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(97)10536-6

The first total synthesis of 25(R)-ruscogenin-1-yl β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranoside (
1), an Ophiopogonis saponin with strong anti-inflammatory and immunopharmacological activities from the tuber of
Liriope muscari (Decne.), is described. The glycosylaton of a highly hindered alcohol by Schmidt's “inverse procedure” is demonstrated.
The total synthesis of the title saponin (
1) was highlighted by a glycosylation of a highly hindered aglycone using Schmidt's “inverse procedure”