Related Experiment Video
Updated: Feb 8, 2026
05:57
Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function
Published on: April 26, 2024
883
Natural product syntheses via carbonylative cyclizations
Kaiqing Ma1, Brandon S Martin2, Xianglin Yin2
1Department of Chemistry, Center for Cancer Research, Institute for Drug Discovery, Purdue University, West Lafayette, Indiana 47907, USA. mjdai@purdue.edu and Modern Research Center for Traditional Chinese Medicine of Shanxi University, No. 92, Wucheng Road, Taiyuan 03006, Shanxi, China.
Natural Product Reports
|June 21, 2018
Summary
This review covers transition metal-catalyzed carbonylative cyclizations used in natural product synthesis from 2000-2018. These methods efficiently construct diverse O-, N-, and carbocyclic ring systems, including ketones and phenols.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Natural products are vital scaffolds for drug discovery.
- Efficient synthetic routes are crucial for accessing complex natural products.
- Transition metal catalysis offers powerful tools for C-C and C-heteroatom bond formation.
Purpose of the Study:
- To review recent advances in natural product total synthesis utilizing transition metal-mediated carbonylative cyclizations.
- To highlight the construction of key O-heterocycles, N-heterocycles, and carbocycles.
- To showcase diverse reaction methodologies for ring system construction.
Main Methods:
- Review of literature from 2000-2018 focusing on transition metal-catalyzed carbonylative cyclizations.
- Categorization of reactions based on the heterocyclic or carbocyclic systems formed.
- Examples include carbonylation of epoxides, lactonization/lactamization, Semmelhack reaction, Pauson-Khand reaction, and Dötz annulation.
Main Results:
- Demonstrated versatility of carbonylative cyclizations in building complex ring systems.
- Successful application in the total synthesis of various natural products.
- Highlighted specific reactions like Stille/Suzuki carbonylation and carbonylative C-H activation.
Conclusions:
- Transition metal-catalyzed carbonylative cyclizations are powerful strategies for natural product synthesis.
- These methods provide efficient access to diverse cyclic structures.
- Continued development in this area promises further advancements in synthetic chemistry.
Related Concept Videos
01:32What is Natural Selection?
129.6K
Natural selection is an evolutionary process in which individuals with survival-promoting traits reproduce at higher rates. These favorable traits become more common within a population or species. Naturally selected traits initially arise via random genetic mutations. In order for selection to occur, there must be variation within a population, the trait controlling the variation must be heritable, and there must be an evolutionary advantage for variation in the trait.
129.6K
01:18Nucleophilic Addition to the Carbonyl Group: General Mechanism
8.5K
The carbonyl carbon in an aldehyde or ketone is the site of a nucleophilic attack due to its electron-deficient nature. Depending on the strength of the incoming nucleophile, the reaction occurs via different mechanistic pathways.
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
8.5K
02:23Alcohols from Carbonyl Compounds: Reduction
12.4K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
12.4K
01:10Nature and Nurture
22.4K
Many human characteristics, like height, are shaped by both nature—in other words, by our genes—and by nurture, or our environment. For example, chronic stress during childhood inhibits the production of growth hormones and consequently reduces bone growth and height. Scientists estimate that 70-90% of variation in height is due to genetic differences among individuals, and 10-30% of variation in height is due to differences in the environments that individuals experience,...
22.4K
01:29IR Frequency Region: Alkene and Carbonyl Stretching
1.3K
Double bonds in alkenes and carbonyl compounds exhibit stretching frequencies in the diagnostic region of the IR spectrum. In addition, alkenes exhibit vinylic C–H stretching and C–H out-of-plane bending absorptions that are useful for identifying substitution patterns.
Stretching frequencies are affected by several factors, such as resonance, inductive effects, ring strain, dipole moment, and hydrogen bonding. Consequently, the stretching frequency of the carbonyl double bond...
Stretching frequencies are affected by several factors, such as resonance, inductive effects, ring strain, dipole moment, and hydrogen bonding. Consequently, the stretching frequency of the carbonyl double bond...
1.3K
01:13Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
3.3K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
3.3K