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Total synthesis of laidlomycin
- Total synthesis of laidlomycin
- Lee, Wonchul; Kang, Sungkyoung; Jung, Byunghyuck; Lee, Hee-Seung; Kang, Sung Ho
- DGIST Authors
- Jung, Byunghyuck
- Issue Date
- Chemical Communications, 52(17), 3536-3539
- Article Type
- 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. © The Royal Society of Chemistry 2016.
- Royal Society of Chemistry
- Related Researcher
Jung, Byung Hyuck
Organic Synthesis; Organo-transition metal chemistry
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