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Total synthesis of laidlomycin

Title
Total synthesis of laidlomycin
Author(s)
Lee, WonchulKang, SungkyoungJung, ByunghyuckLee, Hee-SeungKang, Sung Ho
Issued Date
2016
Citation
Chemical Communications, v.52, no.17, pp.3536 - 3539
Type
Article
Keywords
ALCOHOLSASYMMETRIC EPOXIDATIONCARBOXYLIC-ACIDSMETHYL-ESTERSMONENSINNATURAL-PRODUCTSOXIDATIVE CYCLIZATIONPOLYETHER ANTIBIOTICSSTEREOCONTROLLED TOTAL-SYNTHESISZINC 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.
URI
http://hdl.handle.net/20.500.11750/5151
DOI
10.1039/c5cc10673g
Publisher
Royal Society of Chemistry
Related Researcher
  • 정병혁 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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Appears in Collections:
Department of Physics and Chemistry Asymmetric Organic Synthesis and Drug Synthesis Laboratory 1. Journal Articles

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