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Synthesis of Dimeric Terpenoyl Glycoside Side Chains from Cytotoxic Saponins
Author(s) -
Reicheneder Sabine,
Unverzagt Carlo
Publication year - 2004
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.200352895
Subject(s) - chemistry , glycoside , side chain , stereochemistry , phosphonate , regioselectivity , acylation , saponin , organic chemistry , medicine , polymer , alternative medicine , pathology , catalysis
A bottleneck in the synthesis of the model compound 1 , which bears a dimeric terpenoyl glycoside side chain from cytotoxic saponins, was overcome by the stepwise construction of the terpene part by regioselective acylation of the sugar with a functionalized phosphonate followed by a Horner–Wadsworth–Emmons olefination.
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