Related Experiment Video
Updated: Jan 20, 2026
08:33
Synthesis, Crosslinking and Characterization of Hydrogels
Published on: April 30, 2023
25.0K
Toward the Synthesis of Phormidolides
Alejandro Gil1,2, Michela Giarrusso1,2, Janire Lamariano-Merketegi1,2
1ChemBio Lab, Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain.
ACS Omega
|August 29, 2019
Summary
Researchers developed a stereoselective synthesis for marine natural product phormidolide D. This approach provides key fragments and an advanced intermediate, paving the way for future marine natural product synthesis.
Area of Science:
- Organic Chemistry
- Marine Natural Products Synthesis
Background:
- Phormidolide D (PM D) is a complex marine natural product.
- Existing synthetic strategies for related compounds (PMs A-C) suggest a common structural motif.
Purpose of the Study:
- To develop a convergent and stereoselective synthesis of phormidolide D.
- To prepare key synthetic intermediates, including novel fatty acids.
Main Methods:
- Retrosynthetic analysis dividing PM D into three fragments: macrocyclic core, stapling iodoalkene, and eastern fragment.
- Preparation of fragments 5, 9, and novel fatty acids 7 and 8 with high stereoselectivity.
- Nozaki-Hiyama-Takai-Kishi coupling to join iodoalkene 9 and formylmacrolactone 4.
Main Results:
- Successful preparation of key fragments 5 and 9 with high yields and stereoselectivity.
- Synthesis of previously unreported fatty acids 7 and 8.
- Establishment of the absolute configuration of all stereocenters.
- Generation of an advanced synthetic intermediate via stereocontrolled coupling.
Conclusions:
- A viable synthetic route to phormidolide D has been established.
- Further optimization of protecting groups and reaction conditions for the final step is required.
- The developed retrosynthetic strategy is versatile and applicable to other marine natural products with similar structural features.
Related Concept Videos
01:15Dehydration Synthesis
148.7K
Overview
Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.
Synthesis of carbohydrates
Sugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from...
Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.
Synthesis of carbohydrates
Sugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from...
148.7K
02:17Synthesis and Decomposition Reactions
38.1K
Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.
38.1K
08:33Hydrogel Synthesis
25.0K
Source: Amber N. Barron, Ashlea Patterson, and Taylor D. Sparks, Department of Materials Science and Engineering, The University of Utah, Salt Lake City, UT
Hydrogels are a versatile class of cross-linked polymers produced through relatively simple procedures and with generally inexpensive materials. They can be formed from solution and involve a polymer backbone formed from monomer reagents, an initiator which makes the polymer reactive and a crosslinking species which binds the polymer chains...
Hydrogels are a versatile class of cross-linked polymers produced through relatively simple procedures and with generally inexpensive materials. They can be formed from solution and involve a polymer backbone formed from monomer reagents, an initiator which makes the polymer reactive and a crosslinking species which binds the polymer chains...
25.0K
01:59Lagging Strand Synthesis
61.0K
During replication, the complementary strands in double-stranded DNA are synthesized at different rates. Replication first begins on the leading strand. Replication starts later, occurs more slowly, and proceeds discontinuously on the lagging strand.
There are several major differences between synthesis of the leading strand and synthesis of the lagging strand. 1) Leading strand synthesis happens in the direction of replication fork opening, whereas lagging strand synthesis happens in the...
There are several major differences between synthesis of the leading strand and synthesis of the lagging strand. 1) Leading strand synthesis happens in the direction of replication fork opening, whereas lagging strand synthesis happens in the...
61.0K
02:36Transfer RNA Synthesis
13.2K
One of the unique features of tRNA is the presence of modified bases. In some tRNAs, modified bases account for nearly 20% of the total bases in the molecule. Altogether, these unusual bases protect the tRNA from enzymatic degradation by RNases.
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...
Each of these chemical modifications is carried by a specific enzyme, post-transcription. All of these enzymes have unique base and site-specificity. Methylation, the most common chemical modification, is carried by at least nine different enzymes, with...
13.2K
09:42Solid Phase Synthesis
43.3K
Source: Vy M. Dong and Diane Le, Department of Chemistry, University of California, Irvine, CA
Merrifield's solid-phase synthesis is a Nobel Prize winning invention where a reactant molecule is bound on a solid support and undergoes successive chemical reactions to form a desired compound. When the molecules are bound to a solid support, excess reagents and byproducts can be removed by washing away the impurities, while the target compound remains bound to the resin. Specifically, we will...
Merrifield's solid-phase synthesis is a Nobel Prize winning invention where a reactant molecule is bound on a solid support and undergoes successive chemical reactions to form a desired compound. When the molecules are bound to a solid support, excess reagents and byproducts can be removed by washing away the impurities, while the target compound remains bound to the resin. Specifically, we will...
43.3K