Synthesis of (+)-Hanagokenol
A, (+)-Fortunins E, G, H, and (-)-Sugikurojin
A from Abietic Acid

Enrique Alvarez-Manzaneda; Rachid Chahboun; Esteban Alvarez; Jose M. Ramos; Juan J. Guardia; Ibtissam Messouri; Ikram Chayboun; Ahmed I. Mansour; Abdelaziz Dahdouh

doi:10.1055/s-0030-1258226

PAPER

Synthesis of (+)-Hanagokenol A, (+)-Fortunins E, G, H, and (-)-Sugikurojin A from Abietic Acid

Enrique Alvarez-Manzaneda*^a, Rachid Chahboun^a, Esteban Alvarez^a, Jose M. Ramos^a, Juan J. Guardia^a, Ibtissam Messouri^a, Ikram Chayboun^a, Ahmed I. Mansour^b, Abdelaziz Dahdouh^b
^a Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain
Fax: +34(958)248089; e-Mail: eamr@ugr.es;
^b Laboratoire de Chimie Organique Appliquée, Département de Chimie, Faculté des Sciences, Université Abdelmalek Essaâdi, Tetouan, Morocco

Abstract

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Abstract

A series of 12-hydroxy-substituted abietane diterpenes, functionalized on C19 or C18, have been synthesized starting from 18-hydroxyferruginol. The first synthesis of antibacterial hanagokenol A and fortunins E, G, and H, and a new procedure for preparing sugikurojin A and the immunosuppressive 19-hydroxy-ferruginol are reported.

Key words

antibiotics - diastereoselectivity - phenols - terpenoids - oxidation

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