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Synthesis of Spiro-Isoxazolidine Derivatives of Methyl α-Isocostate

[ Vol. 9 , Issue. 4 ]

Author(s):

Mohamed Zaki*, Abdelouahd Oukhrib, Mohammed Loubidi, Ahmed El Hakmaoui, Marie-Aude Hiebel, Mohammed Akssira and Sabine Berteina-Raboin   Pages 262 - 267 ( 6 )

Abstract:


Background: In recent decades, natural products are an important source of chemotherapeutics as more than half of the effective cancer drugs can be traced to natural origins.

Objective: Moreover, the modification of natural products is one of the most common and fruitful approaches to obtain novel therapeutic agents in medicinal chemistry.

Methods: Continuing with a research project based on the support of Moroccan plant resources. we report herein the use of α-isocostic acid extracted in enantiomerically pure form from Dittrichia viscosa as a convenient starting material for the synthesis of new eudesmane derivatives.

Results: Novel spiro derivatives with a natural scaffold were prepared. Spiro-isoxazolidine derivatives were generated on the exocyclic double bond adjacent to the ester α,β-unsaturated function by 1,3-dipolar cycloaddition of methyl α-isocostate 1 derived from sesquiterpenic isocostic acid, with nitrones 2.

Conclusion: This procedure allowed us to generate enantiomerically pure spiro compounds in one diastereoisomer form with a limited number of steps. These compounds were fully characterized by spectroscopic methods.

Keywords:

Dittrichia viscosa, isocostic acid, terpenes, 1, 3-dipolar cycloaddition, spiro-isoxazolidine, spectroscopic methods.

Affiliation:

Institute of Organic and Analytical Chemistry, Orleans University, UMR CNRS 7311, B.P. 6759, 45067 Orleans Cedex 2, Laboratory of Biomolecular Chemistry Natural Substances and Reactivity (URAC 16), Faculty of Sciences Semlalia, Cadi Ayyad University, B.P. 2390 Marrakech, Institute of Organic and Analytical Chemistry, Orleans University, UMR CNRS 7311, B.P. 6759, 45067 Orleans Cedex 2, Institute of Organic and Analytical Chemistry, Orleans University, UMR CNRS 7311, B.P. 6759, 45067 Orleans Cedex 2, Laboratoire de Chimie Physique & Chimie Bioorganique, Département de Chimie, URA C 22, Pôle RéPAM, FST, Hassan II University of Casablanca, B.P. 146 Yasmina, 28800, Mohammedia, Institute of Organic and Analytical Chemistry, Orleans University, UMR CNRS 7311, B.P. 6759, 45067 Orleans Cedex 2, Institute of Organic and Analytical Chemistry, Orleans University, UMR CNRS 7311, B.P. 6759, 45067 Orleans Cedex 2

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