Latrunculin Analogues with Improved Biological Profiles by "Diverted Total Synthesis": Preparation, Evaluation, and Computational Analysis

• Published in: Chemistry : a European journal Vol. 13; no. 1; pp. 135 - 149
• Main Authors: Fürstner, Alois, Kirk, Douglas, Fenster, Michaël D. B., Aïssa, Christophe, De Souza, Dominic, Nevado, Cristina, Tuttle, Tell, Thiel, Walter, Müller, Oliver
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2007; WILEY‐VCH Verlag; Wiley
• Subjects: actin; Actins - chemistry; Animals; Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis; Bridged Bicyclo Compounds, Heterocyclic - chemistry; Catalysis; chemical biology; Chemistry; Chemistry, Multidisciplinary; computational chemistry; Computer Simulation; Crystallography, X-Ray; Hydrogen Bonding; macrolides; metathesis; Mice; Models, Molecular; Molecular Structure; NIH 3T3 Cells; Physical Sciences; Science & Technology; Thermodynamics; Thiazolidines - chemical synthesis; Thiazolidines - chemistry; total synthesis; CLOSING ALKYNE METATHESIS; SMALL-MOLECULE; CRYSTAL-STRUCTURE; computational chemistry; DISRUPT MICROFILAMENT ORGANIZATION; NUCLEIC-ACIDS; actin; macrolides; CROSS-COUPLING REACTIONS; chemical biology; metathesis; NEGOMBATA-MAGNIFICA DEMOSPONGIAE; EMPIRICAL FORCE-FIELD; total synthesis; STEREOSELECTIVE-SYNTHESIS; GRIGNARD-REAGENTS

Deliberate digression from the blueprint of the total syntheses of latrunculin A (1) and latrunculin B (2) reported in the accompanying paper allowed for the preparation of a focused library of “latrunculin‐like” compounds, in which all characteristic structural elements of these macrolides were sub...