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- W2017442155 abstract "A new enantioselective synthesis of the idolizidine alkaloid (-)-swainsonine 1 in 40% overall yield starting from the known oxazolidinone 6 is described. Throughout the synthesis, the high efficiency of metal-catalyzed reactions is illustrated. The key step is a new ruthenium-catalyzed metathesis rearrangement reaction. In this ring-closing/ring-opening tandem process, stereocenters are transferred from a ring to the olefinic side chain of the formed heterocycle. The metathesis precursor was obtained by palladium-catalyzed desymmetrization of cyclopentenediol. The synthesis was completed by functionalization of the terminal double bond, cyclization of the second ring, and diastereoselective dihydroxylation." @default.
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- W2017442155 date "2002-05-15" @default.
- W2017442155 modified "2023-10-17" @default.
- W2017442155 title "A New Approach to (−)-Swainsonine by Ruthenium-Catalyzed Ring Rearrangement" @default.
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- W2017442155 doi "https://doi.org/10.1021/jo025589u" @default.
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