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Cover Picture: Natural Product‐Guided Synthesis of a Spiroacetal Collection Reveals Modulators of Tubulin Cytoskeleton Integrity (Eur. J. Org. Chem. 22/2005)
Author(s) -
Barun Okram,
Kumar Kamal,
Sommer Stefan,
Langerak Anette,
Mayer Thomas U.,
Müller Oliver,
Waldmann Herbert
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200590044
Subject(s) - aldol reaction , chemistry , tubulin , natural product , cytoskeleton , cover (algebra) , phosphatase , microtubule , solid phase synthesis , stereochemistry , polymerization , stereoselectivity , boron , molecule , total synthesis , combinatorial chemistry , organic chemistry , cell , biochemistry , catalysis , enzyme , microbiology and biotechnology , peptide , mechanical engineering , polymer , engineering , biology
The cover picture shows the stereoselective solid‐phase synthesis of highly substituted spiroketal molecules. Asymmetric aldol reactions on a solid phase are the key steps involved in this synthetic route. Both resin‐bound β‐hydroxy aldehydes and boron enolates were employed for syn ‐ and anti ‐aldol reactions, respectively. Out of this small collection of spiroacetals, some molecules showed activities against tubulin polymerization. The effect of two different spiroketals at a concentration of 5 μ m on the tubulin cytoskeleton is shown in the picture (top right and bottom left). Furthermore, some spiroketals were found to be phosphatase inhibitors. Details are discussed in the article by H. Waldmann et al. on p. 4773 ff.