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A Stereocontrolled Synthesis of the C11-C24 Fragment of InostamycinA via the Desymmetrization of Glycerols

Title
A Stereocontrolled Synthesis of the C11-C24 Fragment of InostamycinA via the Desymmetrization of Glycerols
Authors
Yu, GuangriJung, ByunghyuckLim, SeolheeLee, Hee-SeungKang, Sung Ho
DGIST Authors
Jung, Byunghyuck
Issue Date
2016-01
Citation
Asian Journal of Organic Chemistry, 5(1), 107-113
Type
Article
Article Type
Article
Keywords
DesymmetrizationGlycerolsInstamycinaPhosphatidylinositol Turnover InhibitorsTotal Synthesis
ISSN
2193-5807
Abstract
A robust and reproducible route has been developed for the synthesis of the C11-C24 fragment of inostamycinA. Whilst the core scaffold of this compound was constructed via a series of addition reactions and an aldol condensation, the stereogenic centers were installed via a series of complex reactions involving a diastereoselective desymmetrization for the two quaternary carbons at C16 and C20, a crotylation for the carbons at C17 and C18, an aldol condensation for the carbons at C12 and C13, an allylation for the carbon at C21, and a chiral building block for the installation of the carbon at C14. All of these steps proceeded with high yield and stereoselectivity, and were also scalable. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
http://hdl.handle.net/20.500.11750/5131
DOI
10.1002/ajoc.201500386
Publisher
Wiley-VCH Verlag
Related Researcher
  • Author Jung, Byunghyuck  
  • Research Interests Organic Synthesis; Organo-transition metal chemistry
Files:
There are no files associated with this item.
Collection:
School of Undergraduate Studies1. Journal Articles


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