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

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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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2016-01
Language
English
Article Type
Article
Keywords

SQUAMOUS-CELL CARCINOMA; ENANTIOSELECTIVE SYNTHESIS; INOSITOL TRANSFERASE; ORGANIC-SYNTHESIS; LUNG-CARCINOMA; CDP-DG; INHIBITION; ALCOHOLS; REAGENTS; TRIMETHYLSILYLDIAZOMETHANE

Citation

ASIAN JOURNAL OF ORGANIC CHEMISTRY, v.5, no.1, pp.107 - 113

ISSN
2193-5807
DOI
10.1002/ajoc.201500386
URI
http://hdl.handle.net/10203/207299
Appears in Collection
CH-Journal Papers(저널논문)
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