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Asymmetric Solid‐Phase Synthesis of 6,6‐Spiroketals
Author(s) -
Barun Okram,
Sommer Stefan,
Waldmann Herbert
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.200353609
Subject(s) - aldol reaction , stereoselectivity , yield (engineering) , boron , combinatorial chemistry , chemistry , phase (matter) , solid phase synthesis , key (lock) , organic chemistry , stereochemistry , materials science , computer science , catalysis , biochemistry , computer security , peptide , metallurgy
Structurally simplified spiroketals derived from natural products often retain the biological activity of the parent compound. An asymmetric solid‐phase synthesis with boron‐mediated aldol reactions as key stereodifferentiating transformations provides 6,6‐spiroketals in just 12 steps in high yield and with high stereoselectivity (see scheme). The procedure is suitable for the creation of compound libraries for use in medicinal chemistry.