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Chirality Relay To Access Oxygenated Angular Aromatic Polyketides
Author(s) -
Baranczak Aleksandra,
Sulikowski Gary A.
Publication year - 2009
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.200901712
Subject(s) - pinacol , diol , chemistry , glycosylation , chirality (physics) , stereochemistry , lactone , cleavage (geology) , combinatorial chemistry , organic chemistry , catalysis , biochemistry , biology , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark , paleontology , fracture (geology)
Solution to a difficult problem : The selective glycosylation of one hydroxy group of the pseudo‐ C 2 ‐symmetric trans diol of benanomicin–pradimicin antibiotics presents a significant synthetic challenge. Sequential asymmetric cleavage of a biaryl lactone and pinacol cyclization (see scheme) provide access to these compounds as well as the naphthoxanthene antibiotic FD‐594. The product diol emerges differentially protected from the pinacol coupling.