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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Synthesis of two new hemisynthetic diterpenylhydroquinones from natural ent-labdanes
Luis Espinoza Catalán1, Karen Catalán Marín, Alejandro Madrid Villegas
1Departamento de Química, Universidad Técnica Federico Santa María, Av. España N degrees 1680, Valparaíso, Chile. luis.espinozac@usm.cl
Abstract:
The synthesis and structural determination of two new diterpenylhydroquinones: 2beta-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2beta-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used.
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