Related Experiment Video
Updated: May 9, 2026
09:14
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Total synthesis of lysergic acid
Satoshi Umezaki1, Satoshi Yokoshima, Tohru Fukuyama
1Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Organic Letters
|August 8, 2013
Summary
Researchers achieved the total synthesis of lysergic acid. This breakthrough utilized stereoselective Evans aldol reactions and sequential ring-closing metathesis with intramolecular Heck reactions to build the core structure.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Lysergic acid is a crucial ergot alkaloid precursor.
- Efficient synthetic routes are vital for accessing lysergic acid derivatives.
Purpose of the Study:
- To achieve a total synthesis of lysergic acid.
- To develop a novel and efficient synthetic strategy.
Main Methods:
- Stereoselective construction of stereogenic centers using the Evans aldol reaction.
- Sequential ring-closing metathesis and intramolecular Heck reaction for C and D ring formation.
Main Results:
- Successful total synthesis of lysergic acid.
- Demonstrated the efficacy of the combined synthetic methodologies.
Conclusions:
- The developed synthetic route provides a viable pathway to lysergic acid.
- Highlights the power of modern synthetic organic chemistry techniques.
Related Concept Videos
01:19Formation of Lipopolysaccharides
Lipopolysaccharides (LPS) are crucial components of the outer membrane of Gram-negative bacteria, serving both structural and functional roles. It contributes to membrane stability and protects bacteria from host immune responses. LPS is composed of three major regions—lipid A, a core oligosaccharide, and an O antigen. The biosynthesis and assembly of LPS involve a highly coordinated set of enzymatic reactions and transport mechanisms. Additionally, LPS is recognized as an endotoxin, triggering...
01:25Production of Organic Acids
Lactic acid, an important organic acid extensively applied in food, pharmaceutical, and biodegradable polymer industries, is primarily produced via microbial fermentation. This method is favored over chemical synthesis due to its environmental sustainability and capacity for enantiomerically pure product formation. Among various microbial processes, the fermentation of starch-based substrates stands out due to the abundance and renewability of raw materials like corn and potatoes.Hydrolysis of...
01:27Hallucinogens and Psychedelics
Hallucinogens are psychoactive substances that profoundly alter perceptual experiences, generating unreal visual and sensory images. Often referred to as psychedelic drugs — a term derived from the Greek words "psyche" (mind) and "delos" (revealing) — these substances include marijuana and lysergic acid diethylamide (LSD), among others. These drugs vary in intensity and effects.
Marijuana, derived from the dried leaves and flowers of the hemp plant, contains delta-9-tetrahydrocannabinol (THC)...
Marijuana, derived from the dried leaves and flowers of the hemp plant, contains delta-9-tetrahydrocannabinol (THC)...
01:22CNS Stimulants: Psychedelic Agents
Hallucinogens, also known as psychedelic drugs, are a class of substances known for their ability to alter perception, cognition, and emotions. Despite their profound effects on the mind, these drugs are non-addictive, setting them apart from many other abused substances. The mechanism of action of these drugs lies in their impact on the 5-HT2A receptor in the brain. Upon activation, this receptor couples to Gq-type G proteins, triggering a cascade that releases intracellular calcium. This...
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.
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.