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Related Experiment Video

Updated: Jun 21, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Total synthesis of brevisamide.

Olugbeminiyi O Fadeyi¹, Craig W Lindsley

¹Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37232, USA.

Organic Letters

|July 31, 2009

Summary

Researchers report the second total synthesis of Brevisamide, a marine cyclic ether alkaloid. This streamlined 21-step process efficiently constructs the complex molecule, highlighting a key reductive cyclization for the pyran core.

Area of Science:

Organic Chemistry
Marine Natural Products Chemistry

Background:

Brevisamide is a marine cyclic ether alkaloid isolated from Karenia brevis.
The complex structure of Brevisamide presents a significant synthetic challenge.

Purpose of the Study:

To report the second total synthesis of Brevisamide.
To develop a streamlined and efficient synthetic route to this marine natural product.

Main Methods:

The synthesis involves a 21-step sequence with a longest linear sequence of 14 steps.
A key step utilizes samarium(II) iodide (SmI2) reductive cyclization to form the tetrasubstituted pyran core.

Main Results:

The total synthesis was achieved in 5.2% overall yield.
The streamlined approach successfully constructed the intricate Brevisamide molecule.

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

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Last Updated: Jun 21, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Production and Testing of Antimicrobial Peptides and Their Mimics

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Conclusions:

This work represents a significant advancement in the synthesis of marine alkaloids.
The developed methodology provides an efficient route to Brevisamide and related compounds.