Reagent-controlled domino synthesis of skeletally-diverse compound collections.

An efficient reagent-controlled methodology for generating highly substituted diverse scaffolds from a common substrate has been developed; thus, treatment of a common precursor with different desilylating reagents, such as ammonium fluoride, caesium fluoride and PPTS, triggers different domino reaction sequences, yielding highly substituted pyridines, phenols and benzopyrans, respectively; the substituent patterns of these scaffolds provide further opportunities for library development.

[1]  P. Langer,et al.  Synthesis of chromanes by sequential ‘[3+3]-cyclization/Williamson’ reactions of 1,3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes , 2006 .

[2]  K. Saxena,et al.  Discovery of Mycobacterium Tuberculosis Protein Tyrosine Phosphatase A (MptpA) Inhibitors Based on Natural Products and a Fragment‐Based Approach , 2005, Chembiochem : a European journal of chemical biology.

[3]  Stefan Wetzel,et al.  Cheminformatic Analysis of Natural Products and their Chemical Space , 2007 .

[4]  David R Spring,et al.  Chemical genetics to chemical genomics: small molecules offer big insights. , 2005, Chemical Society reviews.

[5]  A. Sprecher,et al.  The synthesis of pyridine derivatives from 3‐formylchromone , 1981 .

[6]  H. Waldmann,et al.  Solid-Phase Synthesis and Biological Evaluation of a Teleocidin Library—Discovery of a Selective PKCδ Down Regulator , 2000 .

[7]  Herbert Waldmann,et al.  Natural Product-Guided Synthesis of a Spiroacetal Collection Reveals Modulators of Tubulin Cytoskeleton Integrity , 2005 .

[8]  H. Waldmann,et al.  Natural product derived receptor tyrosine kinase inhibitors: identification of IGF1R, Tie-2, and VEGFR-3 inhibitors. , 2002, Angewandte Chemie.

[9]  Herbert Waldmann,et al.  Protein structure similarity clustering and natural product structure as guiding principles in drug discovery. , 2005, Drug discovery today.

[10]  H. Waldmann,et al.  Solid‐Phase Synthesis of Decalin Scaffolds by Robinson Annulation with Immobilised Nazarov Reagents , 2006 .

[11]  H. Waldmann,et al.  Organic Synthesis and Biological Signal Transduction , 1998, Angewandte Chemie.

[12]  P. Arya,et al.  Exploring new chemical space by stereocontrolled diversity-oriented synthesis. , 2005, Chemistry & biology.

[13]  Herbert Waldmann,et al.  Compound library development guided by protein structure similarity clustering and natural product structure. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[14]  Herbert Waldmann,et al.  Asymmetric solid-phase synthesis of 6,6-spiroketals. , 2004, Angewandte Chemie.

[15]  Herbert Waldmann,et al.  Discovery of protein phosphatase inhibitor classes by biology-oriented synthesis. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[16]  H. Waldmann,et al.  Development of natural product-derived receptor tyrosine kinase inhibitors based on conservation of protein domain fold. , 2003, Journal of medicinal chemistry.

[17]  Harald Schwalbe,et al.  Identification of inhibitors for mycobacterial protein tyrosine phosphatase B (MptpB) by biology-oriented synthesis (BIOS). , 2007, Chemistry, an Asian journal.

[18]  Tomohiro Yamaguchi,et al.  The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase , 2006 .

[19]  Derek S. Tan,et al.  Diversity-oriented synthesis: exploring the intersections between chemistry and biology , 2005, Nature chemical biology.

[20]  H. Waldmann,et al.  Stereocomplementary synthesis of a natural product-derived compound collection on a solid phase. , 2006, Chemical communications.

[21]  Herbert Waldmann,et al.  From protein domains to drug candidates-natural products as guiding principles in the design and synthesis of compound libraries. , 2002, Angewandte Chemie.

[22]  Stuart L Schreiber,et al.  Generating Diverse Skeletons of Small Molecules Combinatorially , 2003, Science.

[23]  H. Waldmann,et al.  An Enzyme-Labile Linker Group for Organic Syntheses on Solid Supports. , 1998, Angewandte Chemie.

[24]  Timothy J Mitchison,et al.  Small molecules, big impact: a history of chemical inhibitors and the cytoskeleton. , 2002, Chemistry & biology.

[25]  Waldmann,et al.  Natural Product Synthesis on Polymeric Supports-Synthesis and Biological Evaluation of an Indolactam Library. , 1999, Angewandte Chemie.

[26]  S. Schreiber,et al.  An alkynylboronic ester annulation: development of synthetic methods for application to diversity-oriented organic synthesis. , 2002, Angewandte Chemie.

[27]  Herbert Waldmann,et al.  From protein domains to drug candidates – natural products as guiding principles in , 2002 .

[28]  H. Waldmann,et al.  Stereoselective allylation of aldehydes on solid support and its application in biology-oriented synthesis (BIOS) , 2007 .

[29]  L. Tietze Domino Reactions in Organic Synthesis. , 1996, Chemical reviews.

[30]  H. Waldmann,et al.  Development and biological evaluation of acyl protein thioesterase 1 (APT1) inhibitors. , 2005, Angewandte Chemie.

[31]  Herbert Waldmann,et al.  Natural product-derived modulators of cell cycle progression and viral entry by enantioselective oxa Diels-Alder reactions on the solid phase. , 2007, Chemistry & biology.