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(a) Total synthesis of bryostatin 7: Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407.
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For recent work on BC analogue construction, see: (a) Hale, K. J.; Frigerio, M.; Manaviazar, S.; Hummersone, M. G.; Fillingham, I.; Barsukov, I.; Damblon, C.; Gescher, A.; Roberts, G. C. K. Org. Lett. 2003, 5, 499.
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For other dithiane alkylation strategies for constructing the C(9)-C(10) bond of the bryostatins, see: (a) Vakalopoulos, A.; Lampe, T. F. J.; Hoffmann, H. M. R. Org. Lett. 2001, 3, 929.
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Ref 9
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(b) Ref 9.
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28
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33750039546
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note
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(c) Generally, we have found it more convenient and far less sacrificial to conduct this C-methylation with ketone 9 that has only been recrystallized twice. Generally, two recrystallizations provide material that is approximately 90% pure; the other main contaminant appears to be 1-phenylpentan-2-ol.
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30
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(a) Kocienski, P.; Narquizian, R.; Raubo, P.; Smith, C.; Farrugia, L. J.; Muir, K.; Boyle, F. T. J. Chem. Soc., Perkin Trans. 1 2000, 2357.
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33750035079
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note
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3 reagent with the anomeric OMe would also favor delivery of hydride to the underside of 8 to give 15, but a referee has argued against this proposal on the basis that, if it did occur, it would most likely cause loss of the acid-labile C(9)-OMe.
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For other recent approaches to the AB region of the bryostatins, see: (a) Voight, E. A.; Seradj, H.; Roethle, P. A.; Burke, S. D. Org. Lett. 2004, 6, 4045.
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