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Lab A: Vincent Lindsay, Cyril Nicolas, Pascal Cérat and Sébastien Goudreau Synthesis Meeting Proposed Total Synthesis of Haliclonin A November 7 th, 2009
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2 Retrosynthesis
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3 Phosphonate: Tet. Lett. 1991, 32, 5907 Synthesis of Diels-Alder Precursors HWE: Paintner, F.F.; Bauschke, G.; Polborn, K. Tet. Lett. 2003, 44, 2549
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4 Diels-Alder
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5 Quaternary Center
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6 Macrocyclisation
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7 2nd Macrocycle Chain
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8 vinyl bromide: Tet. Lett. 2004, 45, 2563
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9 Addition of the 2nd Macrocycle Chain
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10 Macrocyclisation & Epoxydation
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11 Double Bond: Radical Deoxygenation-Epoxyde Opening
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12 Epoxyde Opening favorednot favored
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13 Final steps 27 steps
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14 Retrosynthesis
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16 Epoxyde Opening favorednot favored
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