DGIST Scholar: 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

Citation: Yu, Guangri. (2016-01). A Stereocontrolled Synthesis of the C11-C24 Fragment of InostamycinA via the Desymmetrization of Glycerols. Asian Journal of Organic Chemistry, 5(1), 107–113. doi: 10.1002/ajoc.201500386

Author Keywords: desymmetrization ; glycerols ; instamycinA ; phosphatidylinositol turnover inhibitors ; total synthesis

Keywords: ALCOHOLS ; CDP-DG ; Desymmetrization ; ENANTIOSELECTIVE SYNTHESIS ; Glycerols ; INHIBITION ; INOSITOL TRANSFERASE ; Instamycina ; LUNG-CARCINOMA ; ORGANIC-SYNTHESIS ; Phosphatidylinositol Turnover Inhibitors ; REAGENTS ; SQUAMOUS-CELL CARCINOMA ; Total Synthesis ; TRIMETHYLSILYLDIAZOMETHANE

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

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