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de la Torre, M. C.; García, I.; Sierra, M. A. J. Org. Chem. 2003, 68, 6611; and references therein.
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17
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and references therein
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The combination of a Paternò-Büchi reaction and selective oxetane cleavage has found notable application in the synthesis of triquinane natural products. See: Reddy, T. J.; Rawal, V. H. Org. Lett. 2000, 2, 2711; and references therein.
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Recently LDBB has been shown to partially reduce certain electron-deficient aromatic compounds: Donohoe, T. J.; House, D. J. Org. Chem. 2002, 67, 5015. We have not observed formation of any Birch-type products, consistent with the electron-rich nature of the aromatic ring in the systems under investigation.
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23
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8644252205
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note
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Attempted preparation of the photochemical precursor 14 via an analogous sequence of reactions to that described in Scheme 1 was thwarted by the formation of 19 as the major product upon attempted Wittig olefination of 18. Alkene 19 is presumably formed by an initial retro-Michael addition under the reactions conditions to reform ketone 8, which subsequently undergoes Wittig olefination. The sluggish reactivity of hindered aryl ketones to the phosphorus ylide necessitates the high temperature employed, although the difference in reactivity of 2 and 18 under identical reaction conditions is notable. To date, we have been unable to achive methylation of 18 using other methods (Scheme 3). (Diagram presented)
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24
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8644279149
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note
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2Na requires 271.1669). MS (EI): m/z (%) = 248 (54), 218 (20), 217 (95), 187 (44), 161 (42), 135 (100), 105 (19), 95(17), 69 (29) and 41 (11).
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25
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0035813284
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(a) Fukuyama, Y.; Yuasa, H.; Tonoi, Y.; Harada, K.; Wada, M.; Asakawa, Y.; Hashimoto, T. Tetrahedron 2001, 57, 9299.
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Fukuyama, Y.1
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Harada, K.4
Wada, M.5
Asakawa, Y.6
Hashimoto, T.7
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28
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33845378229
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Aristoff, P. A.; Johnson, P. D.; Harrison, A. W. J. Am. Chem. Soc. 1985, 107, 7967.
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Aristoff, P.A.1
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Harrison, A.W.3
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29
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8644240459
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note
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4 and concentrated in vacuo to furnish a pale yellow oil. The crude product was purified by column chromatography (hexane-EtOAc 9:1) to afford 1,13-herbertenediol as a colourless oil (29 mg, 77%). Analytic data agree with those reported in the literature.
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