Journal of Organic Chemistry 2010-09-03

Practical enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis- 4,5-diamino-2-cyclopenten-1-ol derivative.

Bing Wang

Index: J. Org. Chem. 75(17) , 6012-5, (2010)

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Abstract

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.