Synthesis 2010(20): 3493-3503  
DOI: 10.1055/s-0030-1258226
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Enrique Alvarez-Manzaneda*a, Rachid Chahbouna, Esteban Alvareza, Jose M. Ramosa, Juan J. Guardiaa, Ibtissam Messouria, Ikram Chaybouna, Ahmed I. Mansourb, Abdelaziz Dahdouhb
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
Further Information

Publication History

Received 28 May 2010
Publication Date:
20 August 2010 (online)

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.