Total Synthesis of (-) – Uniforine A

Year: 2009

Authors: Parmeggiani C., Martella D., Cardona F., Goti A.

Autors Affiliation: Dipartimento di Chimica Organica “Ugo Schiff”, Laboratorio di Progettazione, Sintesi e Studio di Eterocicli Biologicamente Attivi (HeteroBioLab), Universita` di Firenze, Via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy

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.

Journal/Review: JOURNAL OF NATURAL PRODUCTS

Volume: 72 (11)      Pages from: 2058  to: 2060

More Information: We thank MiUR and Ente Cassa di Risparmio di Firenze, Italy, for financial support. Ente CRF is also acknowledged for granting a 400 MHz NMR spectrometer. Brunella Innocenti and Maurizio Passaponti (Dipartimento di Chimica Organica \”U. Schiff\”) are acknowledged for technical assistance. CINMPIS is gratefully acknowledged for a grant to C.P.
DOI: 10.1021/np900435d

Citations: 32
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