title: Total synthesis of herbimycin A.
abstract: [structure: see text] Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing asymmetric syn-crotylation methodology to introduce the C10, C11, C14, and C15 stereocenters. The C6-C7 stereocenters were introduced using Brown's alpha-pinene-derived gamma-methoxy allylborane reagent. The C12 stereocenter was established by diastereoselective hydroboration.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Kendra D
authors.initials: KD
authors.lastname: Carter
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D008956:Models, Chemical; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D011809:Quinones / Q000138:chemical synthesis*; D017828:Rifabutin / Q000031:analogs & derivatives; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D017646:Organosilicon Compounds; D011809:Quinones; D017828:Rifabutin; C020754:herbimycin