Department of Physics and Chemistry
Asymmetric Organic Synthesis and Drug Synthesis Laboratory
1. Journal Articles
Total synthesis of laidlomycin
- Title
- Total synthesis of laidlomycin
- Author(s)
- Lee, Wonchul ; Kang, Sungkyoung ; Jung, Byunghyuck ; Lee, Hee-Seung ; Kang, Sung Ho
- Issued Date
- 2016
- Citation
- Chemical Communications, v.52, no.17, pp.3536 - 3539
- Type
- Article
- Keywords
- ALCOHOLS ; ASYMMETRIC EPOXIDATION ; CARBOXYLIC-ACIDS ; METHYL-ESTERS ; MONENSIN ; NATURAL-PRODUCTS ; OXIDATIVE CYCLIZATION ; POLYETHER ANTIBIOTICS ; STEREOCONTROLLED TOTAL-SYNTHESIS ; ZINC BOROHYDRIDE
- ISSN
- 1359-7345
- 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. © The Royal Society of Chemistry 2016.
- Publisher
- Royal Society of Chemistry
- Related Researcher
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Jung, Byunghyuck
- Research Interests Organic Synthesis; Organo-transition metal chemistry; Catalytic Asymmetric Synthesis; Synthetic Methodologies; Synthesis of Natural Products and Drugs
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