Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 5, Issue 1, Pages 107-113Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201500386
Keywords
desymmetrization; glycerols; instamycinA; phosphatidylinositol turnover inhibitors; total synthesis
Categories
Funding
- NRF [MSIP 20090083525, 2014R1A5A1011165, 2013R1A2A1A01008358]
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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.
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