The First Total Synthesis of Praecoxin B and Pterocarinin C, Two Natural Products of the Tannin Class

✍ Scribed by Khanbabaee, Karamali ;Lötzerich, Kerstin

• Book ID: 102902553
• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 517 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970738

✦ Synopsis

Abstract

Enantiomerically pure diphenic ester 3 was obtained by esterification of acyl chloride 2 with the glucose derivative 1 by kinetic resolution. Hydrolysis of the ester 3, acylation of the free OH groups at C‐4 and C‐6 of the diol 4 with acid 5 followed by irradiation led to the anomerically deprotected α‐ and β‐anomers (7) (4:1). The natural product praecoxin B (8) was obtained by hydrogenative debenzylation. A second member of the ellagitannin group pterocarinin C (11) was obtained from the common intermediate 7 by acylation in the anomeric position to 10 followed by debenzylation.