Related Experiment Video
Updated: Sep 17, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Total Synthesis of Kavaratamides A-C and Unnatural Analogs
Tomayo I Berida1, Craig W Lindsley1
1Warren Center for Neuroscience Drug Discovery, Department of Pharmacology, Vanderbilt University, Nashville, Tennessee 37067, United States.
Abstract:
Marine cyanobacteria are a rich source of structurally diverse compounds with biological activity. Herein, we report the total synthesis of kavaratamide A (1), a bioactive lipodepsipeptide isolated from Moorena bouillonii. The total synthesis of 1 required 16 steps, with a longest linear sequence of 9 steps, and an overall yield of 2.9%. Our convergent synthetic approach led to the efficient synthesis of kavaratamide A-C, C25-epi-kavaratamide A, and deoxy-kavaratamide A from a common intermediate providing a blueprint for facilitating rapid structure-activity relationship (SAR) studies.
More Related Videos
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis