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

doi:10.1039/C3OB42122H

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

Hanane Bouanou,^a Rubén Tapia,^a M. José Cano,^a Jose M. Ramos,^a Esteban Alvarez,^a Ettahir Boulifa,^b Abdelaziz Dahdouh,^b Ahmed I. Mansour,^b Ramón Alvarez-Manzaneda,^c Rachid Chahboun*^a and Enrique Alvarez-Manzaneda*^a

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^a Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain
E-mail: rachid@ugr.es, eamr@ugr.es
Fax: +34 958 24 80 89
Tel: +34 958 24 80 89

^b Laboratoire de Chimie Organique Appliquée, Département de Chimie, Faculté des Sciences, Université Abdelmalek Essaâdi, Tetouan, Morocco

^c Area de Química Orgánica, Departamento de Química y Física, Universidad de Almería, 04120 Almería, Spain

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.

Organic & Biomolecular Chemistry

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

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

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