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Total synthesis of laidlomycin

Title
Total synthesis of laidlomycin
Authors
Lee, WonchulKang, SungkyoungJung, ByunghyuckLee, Hee-SeungKang, Sung Ho
DGIST Authors
Jung, Byunghyuck
Issue Date
2016
Citation
Chemical Communications, 52(17), 3536-3539
Type
Article
Article Type
Article
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
Files:
There are no files associated with this item.
Collection:
School of Undergraduate Studies1. Journal Articles


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