title: The Total Synthesis of Inostamycin A.
abstract: The first total synthesis of inostamycin A is described. With efficient and stereoselective synthetic routes to aldehyde 3 and ketone 4 developed through asymmetric aldol reactions, addition reactions and reduction, and with chiral building blocks, the two large fragments were coupled with remarkable anti stereoselectivity and efficiency by aldol condensation. The coupling reaction provided the complete carbon skeleton with all the requisite functional groups and stereogenic centers for inostamycin A. The two quaternary carbons at C20 and C16 of ketone 4 were elaborated in a highly stereocontrolled manner by addition reactions of the transmetallated 5 to ethyl ketone 6 and the transmetallated 7 to methyl ketone 8, respectively, in which the use of LaCl3 for transmetallation was critical for high coupling efficiency.
authors.affiliation: Molecular-Level Interface Research Center (MIRC), Department of Chemistry, KAIST, Daejeon, 305-701, Korea.
authors.forename: Guangri
authors.initials: G
authors.lastname: Yu
authors.affiliation: School of Basic Science, DGIST, Daegu, 711-873, Korea.
authors.forename: Byunghyuck
authors.initials: B
authors.lastname: Jung
authors.affiliation: Molecular-Level Interface Research Center (MIRC), Department of Chemistry, KAIST, Daejeon, 305-701, Korea. hee-seung_lee@kaist.ac.kr.
authors.forename: Hee-Seung
authors.initials: HS
authors.lastname: Lee
authors.affiliation: Molecular-Level Interface Research Center (MIRC), Department of Chemistry, KAIST, Daejeon, 305-701, Korea. shkang@kaist.ac.kr.|Center for New Directions in Organic Synthesis (CNOS), Department of Chemistry, Hanyang University, Seoul, 133-791, Korea. shkang@kaist.ac.kr.
authors.forename: Sung Ho
authors.initials: SH
authors.lastname: Kang
mesh_terms: D005663:Furans / Q000138:chemical synthesis; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D005663:Furans; C071861:inostamycin
keywords: aldol reactions; inostamycin A; quaternary stereocenters; retrosynthesis; total synthesis