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For a two-step oxidation of imidazolinone with dimethyldioxirane (DMDO)/N-chlorosuccinimide (NCS) to construct the palau'amine core skeleton, see: a) A. S. Dilley, D. Romo, Org. Lett. 2001, 3, 1535-1538;
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note
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1H NMR spectra of the crude product indicated a clean transformation; however, the cyclization products were not stable to column chromatography on silica gel (among all the isolation conditions examined, Davisil 633 silica gel provided the best yields of the isolated products).
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28
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33645897192
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1,3 strain, see: R. W. Hoffmann, Chem. Rev. 1989, 89, 1841-1860.
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Hoffmann, R.W.1
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33746307753
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For a similar stereospecificity issue, see: Ref. [6]
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For a similar stereospecificity issue, see: Ref. [6].
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33746272124
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note
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A slightly higher temperature (80°C) was required to suppress the formation of the monocyclization product; however, the diastereoselectivity was compromised.
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CCDC-290044 (15) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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