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Synthesis 2008(24): 4019-4027  
DOI: 10.1055/s-0028-1083238
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Synthetic Strategy towards Bioactive Merosesquiterpenoids

Enrique Alvarez-Manzaneda*a, Rachid Chahbouna, Eduardo Cabreraa, Esteban Alvareza, Ali Haidoura, Jose Miguel Ramosa, Ramón Alvarez-Manzanedab, Juan Luis Romeraa, Mari Angeles Escobara, Ibtissam Messouria
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
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Publikationsverlauf

Received 22 July 2008
Publikationsdatum:
01. Dezember 2008 (online)

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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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