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Rapid Total Syntheses Utilizing “Supersilyl” Chemistry
Author(s) -
Albert Brian J.,
Yamaoka Yousuke,
Yamamoto Hisashi
Publication year - 2011
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.201007210
Subject(s) - total synthesis , alkene , chemistry , natural product , cascade , trimethylsilyl , organic chemistry , combinatorial chemistry , stereochemistry , chromatography , catalysis
In short order : The shortest total syntheses of natural product EBC‐23 (see scheme, PMB= para ‐methoxybenzyl, TMS=trimethylsilyl) and a polymethoxy‐1‐alkene to date have been accomplished in just ten total steps each from commercially available chemicals. The syntheses took advantage of highly diastereoselective supersilyl‐directed cascade polyaldol reactions.