A New Synthetic Strategy towards
Bioactive Merosesquiterpenoids

Enrique Alvarez-Manzaneda; Rachid Chahboun; Eduardo Cabrera; Esteban Alvarez; Ali Haidour; Jose Miguel Ramos; Ramón Alvarez-Manzaneda; Juan Luis Romera; Mari Angeles Escobar; Ibtissam Messouri

doi:10.1055/s-0028-1083238

PAPER

A New Synthetic Strategy towards Bioactive Merosesquiterpenoids

Enrique Alvarez-Manzaneda*^a, Rachid Chahboun^a, Eduardo Cabrera^a, Esteban Alvarez^a, Ali Haidour^a, Jose Miguel Ramos^a, Ramón Alvarez-Manzaneda^b, Juan Luis Romera^a, Mari Angeles Escobar^a, Ibtissam Messouri^a
^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 Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Almería, 04120 Almería, Spain

Abstract

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Abstract

The Diels-Alder cycloaddition of the labdane diene methyl trans-communate with various representative dienophiles has been studied. Based on this, a novel strategy for synthesizing bioactive merosesquiterpenes is reported. This methodology affords considerable atom and step economy and makes it feasible to prepare A-ring functionalised compounds. A study on the synthesis of the fungitoxic pycnanthuquinone C has been carried out.

Key words

Diels-Alder reactions - esters - natural products - quinones - terpenoids

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