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.
Total Synthesis of (-)-Uniflorine A / C. PARMEGGIANI; D. MARTELLA; F. CARDONA; A. GOTI. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - STAMPA. - 72:(2009), pp. 2058-2060. [10.1021/np900435d]
Total Synthesis of (-)-Uniflorine A
PARMEGGIANI, CAMILLA;MARTELLA, DANIELE;CARDONA, FRANCESCA;GOTI, ANDREA
2009
Abstract
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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