Related Experiment Video
Updated: Feb 7, 2026
13:42
Gold Nanoparticle Synthesis
Published on: July 10, 2021
15.9K
First total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide
A S Kende1, J I Hernando, J B Milbank
1Department of Chemistry, University of Rochester, Rochester, NY 14627, USA. kende@chem.rochester.edu
Organic Letters
|August 3, 2001
Summary
This study details the total synthesis of stemonamide and isostemonamide alkaloids. Key steps involved N-acyliminium ion chemistry and spirocyclization for constructing complex tetracyclic structures.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Tetracyclic alkaloids like stemonamide and isostemonamide are complex natural products.
- Efficient synthetic routes are crucial for accessing these compounds and their analogs.
Purpose of the Study:
- To achieve the total synthesis of stemonamide and isostemonamide.
- To develop a novel synthetic strategy employing key C-C bond-forming reactions.
Main Methods:
- Utilized a silyloxyfuran and N-acyliminium ion reaction as a key step.
- Employed intramolecular aldol spirocyclization to establish a quaternary center.
- Incorporated Mannich reaction and intramolecular nucleophilic displacement for ring construction.
Main Results:
- Successfully synthesized stemonamide and isostemonamide.
- Demonstrated the efficacy of the developed synthetic pathway.
- Established a robust method for constructing the tetracyclic core.
Conclusions:
- The total synthesis of stemonamide and isostemonamide was accomplished.
- The synthetic strategy highlights the utility of N-acyliminium ion chemistry and spirocyclization.
- This work provides a valuable framework for the synthesis of related alkaloids.
Related Concept Videos
01:15Dehydration Synthesis
150.1K
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...
150.1K
02:17Synthesis and Decomposition Reactions
38.3K
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.
38.3K
01:59Lagging Strand Synthesis
61.4K
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...
61.4K
02:36Transfer RNA Synthesis
13.4K
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...
13.4K
01:12Total Voids in Concrete
492
Total voids in concrete encompass gel water volume, capillary pores, and entrapped air. Gel water (retained within the cement hydration products) and physically entrapped or adsorbed water are significant for the hydration process. For complete hydration, it's estimated that the space needed for the products of a cubic centimeter of cement doubles. Capillary pores constitute the unoccupied space within the hydrated cement paste, with their size largely influenced by the water-to-cement...
492
01:05Total Internal Reflection Fluorescence Microscopy
13.4K
Total internal reflection fluorescence microscopy or TIRF is an advanced microscopic technique used to visualize fluorophores in samples close to a solid surface with a higher refractive index, such as a glass coverslip. TIRF only allows fluorophores in proximity to the solid surface to be excited. When light from a medium with a lower refractive index (such as air) hits the glass coverslip at a critical angle, the light undergoes total internal reflection stead of passing through the glass.
13.4K