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12444277266
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note
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Attempts to generate the acyclic enol ether using other alkylidene reagents (Tebbe, Petasis, Takeda) were also unsuccessful.
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24
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0000091226
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The Tebbe reagent has been used to carry out related cyclizations. (a) Stille, J. R.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 855.
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28
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0037026010
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For a related transformation that utilizes the Takeda protocol see: Uehara, H.; Oishi, T.; Inoue, M.; Shoji, M.; Nagumo, Y.; Kosaka, M.; Le Brazidec, J.-Y.; Hirama, M. Tetrahedron 2002, 58, 6493.
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29
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0037017749
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Mechanistically, we believe that cyclic product results from an olefin metathesis, carbonyl olefination sequence. Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron 2002, 58, 1997.
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30
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12444333594
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note
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3) into 15 in an unoptimized 60% yield using the Grubbs 2 catalyst.
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31
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12444296499
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note
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At present, we do not have a clear explanation for the facial selectivity in the DMDO oxidation of 15. Sasaki observed similar selectivity in the hydroboration of a related oxepene in his gambierol work.4a,b
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32
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