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Practical Enantiospecific Synthesis of an Orthogonally Protected 1,4-<i>trans</i>-1,5-<i>cis</i>- 4,5-Diamino-2-cyclopenten-1-ol Derivative

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An enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis-4,5-diamino-2-cyclopenten-1-ol derivative 16 is reported. The trans-diamine moiety was established by anti-specific vinyl addition to a novel threitol-derived tert-butanesulfinylimine 2 and Overman rearrangement. The cyclopentene skeleton was constructed via RCM reaction of a key 1,6-diene intermediate 11.

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2016-02-24
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