title: Total synthesis of herbimycin A.
abstract: Benzoquinone ansamycin antibiotic herbimycin A was synthesized in 19 linear steps and 4.2% yield. Highlighted is the design of a chiral γ-lactone as the C11-C15 synthon that enabled a facile catalytic asymmetric synthesis of the challenging C8-C20 fragment of the target molecule. The easy access to the stereogenic centers and high overall yield made the strategy applicable in the molecular editing of benzoquinone ansamycins.
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences , No. 1 Xiannongtan Street, Beijing 100050, China.
authors.forename: Rui
authors.initials: R
authors.lastname: Yan
authors.forename: Chuancai
authors.initials: C
authors.lastname: Bian
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Yu
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D017828:Rifabutin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D007783:Lactones; D017828:Rifabutin; C004532:quinone; C020754:herbimycin