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The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B†
Hanane Bouanou,Rubén Tapia,M. José Cano,Jose M. Ramos,Esteban Alvarez,Ettahir Boulifa,Abdelaziz Dahdouh,Ahmed I. Mansour,Ramón Alvarez-Manzaneda,Rachid Chahboun,Enrique Alvarez-Manzaneda
Organic & Biomolecular Chemistry Pub Date : 11/19/2013 00:00:00 , DOI:10.1039/C3OB42122H
Abstract

A very efficient method for synthesizing spirolactones is reported. Treatment of δ,ε-unsaturated carboxylic acids with iodine and triphenylphosphine under mild conditions leads to the corresponding spiro γ-lactones in high yield and with complete stereoselectivity. Utilizing this, the first synthesis of the terpene spirolactones (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B has been achieved.

Graphical abstract: The first synthesis of (−)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B
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