title: Synthesis and structural reconfirmation of bacillamide B.
abstract: A concise total synthesis of the natural product bacillamide B was accomplished in 30% overall yield starting from L-cystine. The key step was a one-pot four-step process of thiazoline formation via a cascade disulfide cleavage/thiocarbonylation/Staudinger reduction/aza-Wittig reaction using β-azido disulfide and carboxylic acid as substrates. The absolute configuration of the natural bacillamide B was reconfirmed to be S and the specific optical rotation was revised to (-).
authors.affiliation: State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
authors.forename: Xue
authors.initials: X
authors.lastname: Sun
authors.forename: Yi
authors.initials: Y
authors.lastname: Liu
authors.forename: Jun
authors.initials: J
authors.lastname: Liu
authors.forename: Guofeng
authors.initials: G
authors.lastname: Gu
authors.forename: Yuguo
authors.initials: Y
authors.lastname: Du
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D019344:Lactic Acid / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D014363:Tryptamines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001688:Biological Products; D013844:Thiazoles; D014363:Tryptamines; C525339:bacillamide B; D019344:Lactic Acid