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Total Synthesis of (+)‐Davidiin
Author(s) -
Kasai Yusuke,
Michihata Naoki,
Nishimura Hidehisa,
Hirokane Tsukasa,
Yamada Hidetoshi
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203305
Subject(s) - chemistry , steric effects , aryl , anomer , chirality (physics) , stereochemistry , axial chirality , glycosyl , total synthesis , ellagitannin , enantioselective synthesis , alkyl , organic chemistry , catalysis , polyphenol , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , antioxidant , quark
Quite strained : The total synthesis of (+)‐davidiin, an ellagitannin with more substituents in axial than in equatorial positions, requires a conformational lock of the glucose, induced by steric repulsion between adjacent bulky silyloxy groups. This conformational lock played a pivotal role in 1) the β‐selective formation of the glycosyl ester at the anomeric position, 2) the formation of the 1,6‐HHDP bridge, and 3) the complete control of axial chirality in the aryl–aryl coupling.