title: Total synthesis of laidlomycin.
abstract: The synthesis of laidlomycin is described. With an established stereocontrolled synthetic route to the aldehyde 5, the known β-keto phosphonate 4 was coupled with 5 and the resulting enone was subjected to a sequential hydrogenolysis/hydrogenation and equilibration process to effect the correct spiroketalization for the natural product. The stereogenic carbons were elaborated by desymmetrization for C12, allylation for C13, vanadyl-induced epoxidation for C16, Zn(BH4)2 reduction for C17, a chiral building block for C18 and C24, Shi epoxidation for C20 and C21, Myers' alkylation for C22, and thermodynamic control for C25.
authors: MIRC, Department of Chemistry, KAIST, Daejeon 34141, Korea. hee-seung_lee@kaist.ac.kr shkang@kaist.ac.kr.
authors: Wonchul
authors: W
authors: Lee
authors: Sungkyoung
authors: S
authors: Kang
authors: Byunghyuck
authors: B
authors: Jung
authors: Hee-Seung
authors: HS
authors: Lee
authors: Sung Ho
authors: SH
authors: Kang
mesh_terms: D008985:Monensin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D008985:Monensin; C010208:laidlomycin