4.7 Article

Total Synthesis of (-)-Uniflorine A

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 72, Issue 11, Pages 2058-2060

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/np900435d

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Funding

  1. MiUR
  2. Ente Cassa di Risparmio di Firenze, Italy
  3. CINMPIS

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Total synthesis of (-)-uniflorine A (3) has been accomplished in nine steps and 11% overall yield from carbohydrate-based nitrone 5. The key steps of the synthetic strategy were a high regio- and complete stereoselective 1,3-dipolar cycloaddition of alkene 6 with nitrone 5, a Tamao-Fleming reaction for replacing the silicon substituent with a hydroxy group with retention of configuration, and a Mitsunobu reaction to establish the correct configuration of the target molecule at C-6.

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