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A C2,C2′-bis-isopropyl ether was utilized in the epoxide opening in the first-generation synthesis of cercosporin 3, which is detailed in the next paper of this series (DOI: 10.1021/jo9013854).
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Broka in ref 6a reported long reaction times (3 d) in cleaving TBDPS ethers (present in the C7,C7′-substitution) of a biaryl similar to 71. In addition, the oxidative cyclization to the perylenequinone stalled at the hydroperylenequinone when the TBDPS groups were present.
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For further details on the optimization of the palladium-catalyzed O-arylation and the rhodium-mediated decarbonylation, see the next paper in this series (DOI: 10.1021/jo9013854).
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For further details on the optimization of the palladium-catalyzed O-arylation and the rhodium-mediated decarbonylation, see the next paper in this series (DOI: 10.1021/jo9013854).
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73449107345
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For further details on the sensitivity of different functional groups to PIFA, see the next paper in this series DOI: 10.1021/jo9013854
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For further details on the sensitivity of different functional groups to PIFA, see the next paper in this series (DOI: 10.1021/jo9013854).
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96
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73449111924
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See Scheme 16 in the preceding paper of this series: Mulrooney, C.; Morgan, B. J.; Li, X.; Kozlowski, M. C. J. Org. Chem. 2010, 75 (DOI: 10.1021/jo9013832).
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See Scheme 16 in the preceding paper of this series: Mulrooney, C.; Morgan, B. J.; Li, X.; Kozlowski, M. C. J. Org. Chem. 2010, 75 (DOI: 10.1021/jo9013832).
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