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.
