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.
Method:
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.