De novo synthesis of teleocidin B analogs

• Published in: Tetrahedron Vol. 66; no. 11; pp. 1963 - 1972
• Main Authors: Pu, Jun, Deng, Kangwen, Butera, John, Chlenov, Michael, Gilbert, Adam, Kagan, Mike, Mattes, James, Resnick, Lynn
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 13.03.2010; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Claisen rearrangement; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Intramolecular Heck reaction; Organic chemistry; Physical Sciences; Preparations and properties; Ruthenium catalyzed indole cyclization; Science & Technology; Teleocidin B; Ruthenium catalyzed indole cyclization; Teleocidin B; Claisen rearrangement; Intramolecular Heck reaction; SIGNAL-TRANSDUCTION; PROTEIN-KINASE-C; TUMOR PROMOTER TELEOCIDINS; CELLULAR-REGULATION; PALLADIUM-CATALYZED ARYLATION; BIOLOGICAL EVALUATION; TOXIC SUBSTANCE; LYNGBYATOXIN-A; Intramolecular reaction; Catalytic reaction; Nitrogen heterocycle; Heck reaction; Ruthenium II; Alkene; Amine; Cyclization; Analog; Aromatic compound; Inhibitor; Indole derivatives; Chemical synthesis; Ethylenic compound; Ruthenium complex
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.01.048

Teleocidin B analogs have been synthesized in 24 steps and 1.9% overall yield. The key steps include aromatic Claisen rearrangement, intramolecular Heck reaction of a tetra-substituted alkene, and ruthenium (II) catalyzed indole cyclization. Teleocidin and the new analogs promote cell spreading on fibroblast cells that were treated with amino-Nogo, an inhibitor of cell spreading. Teleocidin B analogs were prepared in 24 steps. Key steps include an aromatic Claisen rearrangement, an intramolecular Heck reaction of a tetra-substituted alkene, and a ruthenium catalyzed cyclization indole formation. [Display omitted]