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Total synthesis of (-)-aplaminal.

Amos B Smith¹, Zhuqing Liu

¹Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.

Organic Letters

|August 30, 2008

Summary

Researchers achieved the total synthesis of (-)-aplaminal, a cytotoxic sea hare metabolite with a unique triazobicyclo[3.2.1]octane structure. This 9-step synthesis establishes the compound's absolute configuration and provides a viable route for further study.

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Area of Science:

Organic Chemistry
Marine Natural Products
Synthetic Methodology

Background:

(-)-Aplaminial is a cytotoxic metabolite isolated from a sea hare.
The molecule possesses a complex and unique triazobicyclo[3.2.1]octane skeleton.
Elucidation of its absolute configuration is crucial for understanding its biological activity.

Purpose of the Study:

To achieve the total synthesis of (-)-aplaminal.
To assign the absolute configuration of (-)-aplaminal.
To develop a synthetic strategy for accessing the triazobicyclo[3.2.1]octane core.

Main Methods:

The synthesis commenced with the condensation of a monoprotected diamine and dimethyl 2-oxomalonate to form the imidazolidine core.
Introduction of the third nitrogen was accomplished through Mitsunobu activation and azide displacement.
Subsequent reduction and lactam formation using AlMe3 yielded the target molecule.

Main Results:

The total synthesis of (-)-aplaminal was successfully completed in 9 steps.
An overall yield of 19% was achieved for the synthetic route.
The absolute configuration of (-)-aplaminal was definitively assigned.

Conclusions:

The total synthesis of (-)-aplaminal provides a reliable method for its preparation.
This work confirms the structure and absolute configuration of this cytotoxic marine natural product.
The developed synthetic strategy may be applicable to other complex nitrogen-containing heterocycles.