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  • Title: Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: total synthesis of (+)-streptazolin.
    Author: Li F, Warshakoon NC, Miller MJ.
    Journal: J Org Chem; 2004 Dec 10; 69(25):8836-41. PubMed ID: 15575765.
    Abstract:
    Concise total syntheses of (+)-streptazolin 1 and its more stable dihydro derivative 2 were accomplished via an intramolecular aldol condensation strategy starting from readily available aminocyclopentenol (-)-7. The synthetic sequence included reductive amination, stereoselective epoxidation, intramolecular aldol (and condensation) reaction, and Wittig reaction. The overall yield for dihydro derivative 2 from aminocyclopentenol (-)-7 was about 7% for a total of 14 steps.
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