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45
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5444250285
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note
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1H NMR and HRMS (ESI). The MS data confirmed the molecular formula and allowed at least some NMR assignments to be made. We found it essentially impossible to confirm the identity of reaction products using NMR as the sole method of characterization.
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46
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5444275585
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note
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2O, 25 °C, 87%] to afford the quinone 48, thereby validating the feasibility of maintaining the integrity of the aziridine ring system through this reaction sequence. (Diagram presented)
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47
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5444255451
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note
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It proved impossible to remove a pyrrolidine tert-butyl carbamate once the C10 carbamate and/or the quinone were installed; intermediates possessing a benzyl carbamate protecting the pyrrolidine nitrogen could be converted to a quinone bearing system.
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48
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0033591940
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He, F.; Bo, Y.; Altom, J. D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 6771.
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49
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5444267838
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note
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Comparable syntheses of 1 or a closely related compound have required 32 total steps (20 linear)13a or 27 steps (27 linear).13b
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