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
- Author(s)
- Yu, Guangri ; Jung, Byunghyuck ; Lim, Seolhee ; Lee, Hee-Seung ; Kang, Sung Ho
- DGIST Authors
- Jung, Byunghyuck
- Issued Date
- 2016-01
- Type
- Article
- Article Type
- Article
- Keywords
- ALCOHOLS ; CDP-DG ; Desymmetrization ; Desymmetrization ; ENANTIOSELECTIVE SYNTHESIS ; Glycerols ; Glycerols ; INHIBITION ; INOSITOL TRANSFERASE ; Instamycina ; Instamycina ; LUNG-CARCINOMA ; ORGANIC-SYNTHESIS ; Phosphatidylinositol Turnover Inhibitors ; Phosphatidylinositol Turnover Inhibitors ; REAGENTS ; SQUAMOUS-CELL CARCINOMA ; Total Synthesis ; Total Synthesis ; TRIMETHYLSILYLDIAZOMETHANE
- 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
- Publisher
- Wiley-VCH Verlag
- Related Researcher
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Jung, Byunghyuck 화학물리학과
- 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:
- School of Undergraduate Studies 1. Journal Articles
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