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- W2016162570 abstract "An efficient, modular, asymmetric synthesis of penaresidin A is disclosed. A β-protected amino-γ,δ-unsaturated sulfoxide was prepared by stereoselective addition of the lithio anion of (R)-methyl p-tolyl sulfoxide to an unsaturated sulfinylimine. The pendant sulfoxide group was used as an intramolecular nucleophile to functionalize an alkene regio- and stereoselectively to furnish a bromohydrin, which was employed as the key intermediate in the preparation of the azetidine subunit of penaresidin A. The stereogenic centers of the side chain were introduced by a regioselective opening of an epoxide. Julia−Kocienski olefination was used to couple the azetidine and side chain subunits. The methodology disclosed herein is also useful for the synthesis of ribo- and arabino-phytosphingosines and compounds possessing the amino alcohol moiety." @default.
- W2016162570 created "2016-06-24" @default.
- W2016162570 creator A5031662314 @default.
- W2016162570 creator A5019933368 @default.
- W2016162570 date "2009-12-21" @default.
- W2016162570 modified "2023-10-09" @default.
- W2016162570 title "An Efficient Stereoselective Synthesis of Penaresidin A from (<i>E</i>)-2-Protected Amino-3,4-unsaturated Sulfoxide" @default.
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- W2016162570 doi "https://doi.org/10.1021/jo9022638" @default.
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