Related Experiment Video
Updated: Jun 27, 2026
09:10
Synthesis of Masarimycin, a Small Molecule Inhibitor of Gram-Positive Bacterial Growth
Published on: January 7, 2022
Total synthesis of (+)-neomarinone
Miguel Peña-López1, M Montserrat Martínez, Luis A Sarandeses
1Departamento de Química Fundamental, Universidade da Coruña, Campus Zapateira, s/n; 15071A Coruña, Spain.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 5, 2008
Summary
The first total synthesis of (+)-neomarinone, a complex natural product, was successfully achieved. This study confirms the molecule's stereochemistry using chiral building blocks and advanced synthetic reactions.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- (+)-Neomarinone is a marine natural product with a unique furanonaphthoquinone structure.
- The total synthesis of such complex molecules presents significant chemical challenges.
Purpose of the Study:
- To achieve the first total synthesis of (+)-neomarinone.
- To confirm the relative and absolute stereochemistry of natural neomarinone.
Main Methods:
- Utilized a concise and convergent synthetic strategy.
- Employed methyl (R)-lactate and (R)-3-methylcyclohexanone as chiral building blocks.
- Key reactions included diastereoselective 1,4-conjugate addition, enolate alkylation, and a regioselective Diels-Alder reaction.
Main Results:
- Successfully synthesized (+)-neomarinone.
- Stereocontrolled formation of two quaternary stereocenters was achieved.
- The furanonaphthoquinone skeleton was constructed efficiently.
Conclusions:
- The first total synthesis of (+)-neomarinone is reported.
- The synthetic route validates the proposed stereochemistry of the natural product.
Related Concept Videos
01:29Biosynthesis of Lipids
Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis pathway, which...
01:14Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
01:28Biosynthesis of Nucleic Acids
Nucleic acid biosynthesis is a fundamental biochemical process that produces the purine and pyrimidine nucleotides essential for DNA and RNA synthesis. This pathway maintains a balanced nucleotide pool, preventing imbalances that could jeopardize genetic integrity and cellular function. Given the crucial role of nucleotides, their synthesis is tightly regulated to ensure proper cellular homeostasis.Purine BiosynthesisThe biosynthesis of purine nucleotides begins with ribose-5-phosphate, a...
01:24Biosynthesis in Bacteria
Biosynthesis in bacteria is a fundamental anabolic process that generates essential macromolecules, including proteins, nucleic acids, lipids, and polysaccharides. These macromolecules are critical for cellular growth, replication, and function. The process is tightly regulated and energetically linked to catabolic pathways to ensure optimal resource utilization.Biosynthetic pathways begin with precursor metabolites such as pyruvate, acetyl-CoA, and glucose-6-phosphate derived from glycolysis,...
03:02Organic Compounds
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
01:29Amino Acid Biosynthetic Pathways
Amino acid biosynthesis is essential for cell growth, protein synthesis, and metabolic regulation. Cells generate essential and non-essential amino acids from metabolic intermediates to sustain vital biological functions. These intermediates originate from key metabolic pathways: glycolysis, the tricarboxylic acid (TCA) cycle, and the pentose phosphate pathway. Important precursors include α-ketoglutarate, pyruvate, oxaloacetate, phosphoenolpyruvate, and erythrose-4-phosphate, which provide...