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2690 We have also reported the formal total synthesis of (-)-morphine by the sequential Claisen rearrangement starting from d-glucal; see: Tetrahedron Lett. 2008, 49, 358-362
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Hama, N.; Matsuda, T.; Sato, T.; Chida, N. Org. Lett. 2009, 11, 2687-2690 We have also reported the formal total synthesis of (-)-morphine by the sequential Claisen rearrangement starting from d-glucal; see: Tanimoto, H.; Saito, R.; Chida, N. Tetrahedron Lett. 2008, 49, 358-362
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We reported orthoamide-type Claisen rearrangements of allylic diols, which was successfully applied to the total synthesis of (-)-kainic acid; see:;
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We reported orthoamide-type Claisen rearrangements of allylic diols, which was successfully applied to the total synthesis of (-)-kainic acid; see: Kitamoto, K.; Sampei, M.; Nakayama, Y.; Sato, T.; Chida, N. Org. Lett. 2010, 12, 5756-5759
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For total syntheses of broussonetines, see:;
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For total syntheses of broussonetines, see: Yoda, H.; Shimojo, T.; Takabe, K. Tetrahedron Lett. 1999, 40, 1335-1336
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The sequential Overman rearrangement of bistrichloroimidate 18 provided bistrichloroacetamide i in 92% yield.
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The sequential Overman rearrangement of bistrichloroimidate 18 provided bistrichloroacetamide i in 92% yield.
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30
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79951641756
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Overman rearrangement of MOM-protected trichloroacetoimidate ii, which was synthesized from 16 in four steps, proceeded at lower temperature and much faster than the orthoamide version. As Danishefsky reported in ref 5b, we also observed that two diastereomers of orthoamide 19 underwent equilibration at room temperature.
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Overman rearrangement of MOM-protected trichloroacetoimidate ii, which was synthesized from 16 in four steps, proceeded at lower temperature and much faster than the orthoamide version. As Danishefsky reported in ref 5b, we also observed that two diastereomers of orthoamide 19 underwent equilibration at room temperature.
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We believe that BHT might suppress the decomposition pathway via a radical species.
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We believe that BHT might suppress the decomposition pathway via a radical species.
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Synthesis of vinyl iodide 12 is described in the Supporting Information.
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Synthesis of vinyl iodide 12 is described in the Supporting Information.
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