Modular Asymmetric Synthesis of Aigialomycin D, a Kinase-Inhibitory Scaffold

On solid ground: Despite no obvious resemblance to adenosine analogues, the family of resorcyclic macrolides contains a high proportion of kinase and ATPase inhibitors. A solid‐phase total synthesis of aigialomycin D extends the diversity of this class of natural product. Aigialomycin was found to i...

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Published inAngewandte Chemie International Edition Vol. 45; no. 24; pp. 3951 - 3954
Main Authors Barluenga, Sofia, Dakas, Pierre-Yves, Ferandin, Yoan, Meijer, Laurent, Winssinger, Nicolas
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 12.06.2006
WILEY‐VCH Verlag
Wiley
Wiley-VCH Verlag
Subjects
Antimalarials
Antimalarials - chemical synthesis
Antimalarials - chemistry
Biochemistry, Molecular Biology
Chemistry
Chemistry, Multidisciplinary
Life Sciences
Macrolides
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
natural products
Phosphotransferases
Phosphotransferases - antagonists & inhibitors
Physical Sciences
protein kinase inhibitors
Science & Technology
solid-phase synthesis
total synthesis
HSP90
POCHONIN-C
METATHESIS CATALYSTS
RADICICOL
protein kinase inhibitors
STEREOCHEMISTRY
HYPOTHEMYCIN
OLEFIN METATHESIS
solid-phase synthesis
MACROLIDES
natural products
GELDANAMYCIN
CHEMISTRY
total synthesis
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Summary:On solid ground: Despite no obvious resemblance to adenosine analogues, the family of resorcyclic macrolides contains a high proportion of kinase and ATPase inhibitors. A solid‐phase total synthesis of aigialomycin D extends the diversity of this class of natural product. Aigialomycin was found to inhibit CDK1/5 and GSK. EOM=ethoxymethyl.
Bibliography:istex:C8FE5C6225A39E7C0B60FC770C37FFB1A6483811
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ArticleID:ANIE200600593
This project was partly supported by grants from the ARC (3683 to N.W.), the EEC (FP6-2002-Life Sciences & Health, PRO-KINASE Research Project to L.M. and MIRG-CT-2004-505317 to N.W.), and the Human Frontier Science Program (HFSP 0080/2003 to N.W.). A MENRT fellowship (P.-Y.D.) is also gratefully acknowledged. The authors thank Niels Reichardt for preliminary work on this project.
This project was partly supported by grants from the ARC (3683 to N.W.), the EEC (FP6‐2002‐Life Sciences & Health, PRO‐KINASE Research Project to L.M. and MIRG‐CT‐2004‐505317 to N.W.), and the Human Frontier Science Program (HFSP 0080/2003 to N.W.). A MENRT fellowship (P.‐Y.D.) is also gratefully acknowledged. The authors thank Niels Reichardt for preliminary work on this project.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200600593