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

Khanbabaee Karamali | Zendy; Lötzerich Kerstin | Zendy

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

Author(s) -

Khanbabaee Karamali,

Lötzerich Kerstin

Publication year - 1997

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199719970738

Subject(s) - chemistry , acylation , anomer , ellagitannin , hydrolysis , kinetic resolution , organic chemistry , tannin , derivative (finance) , chloride , stereochemistry , catalysis , enantioselective synthesis , economics , antioxidant , polyphenol , food science , financial economics

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.

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