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.
2009
72
2058
2060
C. PARMEGGIANI; D. MARTELLA; F. CARDONA; A. GOTI
File in questo prodotto:
File Dimensione Formato  
UniflorineJNATPROD2009.pdf

Accesso chiuso

Tipologia: Versione finale referata (Postprint, Accepted manuscript)
Licenza: Tutti i diritti riservati
Dimensione 165.19 kB
Formato Adobe PDF
165.19 kB Adobe PDF   Richiedi una copia

I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/368057
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 33
  • ???jsp.display-item.citation.isi??? 32
social impact