New Approach to the Synthesis of the Natural Product Aripuanin

Abstract

Aripuanin is a megastigmane that exists in the leaves of Ficus aripuanensis C.C. Berg (Moraceae). The present study describes a new approach to the total synthesis of this natural product starting from the readily available β-ionone. The proposed synthetic route provided racemic aripuanin in moderate yields (~31%). This route can be applied to the synthesis of other natural products bearing the megastigmane moiety, as well as to the enantioselective synthesis of aripuanin derivatives.

GRAPHICAL ABSTRACT

Keywords:

• Aripuanin
• Ficus aripuanensis
• megastigmane
• natural product
• synthesis

ACKNOWLEDGMENT

The authors gratefully acknowledge Dr. Marilda D. Assis (DQ-FFCLRP-USP) for supplying the catalyst Mn(salen).

SUPPLEMENTARY INFORMATION

Full experimental details, characterization data for all compounds, and copies of the ¹H and ¹³C NMR spectra for this article can be accessed on the publisher’s website.