4.5 Article

Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties

Related references

Note: Only part of the references are listed.
Review Biochemistry & Molecular Biology

Fukuyama reduction, Fukuyama coupling and Fukuyama-Mitsunobu alkylation: recent developments and synthetic applications

Sana Sikandar et al.

Summary: The Fukuyama reaction is an important method for the synthesis of multifunctional aldehydes, secondary amines, and ketones due to its mild reaction conditions. The use of thioesters in this reaction is attractive for organic chemists as they are easily accessible from corresponding carboxylic acids. The Fukuyama-Mitsunobu reaction utilizes 2-nitrobenzenesulfonyl (Ns) for the protection/activation/deprotection of primary amines to afford secondary amines in good yields and high enantioselectivities.

MOLECULAR DIVERSITY (2022)

Review Chemistry, Organic

Synthesis and Reactivity of Uhle's Ketone and Its Derivatives

Francesca Bartoccini et al.

Summary: Uhle's ketone and its derivatives serve as versatile intermediates for synthesizing a variety of 3,4-fused tricyclic indole frameworks, which are important in the fields of synthetic organic chemistry and medicinal chemistry. The preparation methods can be roughly classified into two categories, and the reactivity mainly comes from the electrophilicity of the carbonyl carbon or the acidity of the alpha-hydrogen.

SYNTHESIS-STUTTGART (2021)

Review Chemistry, Multidisciplinary

The Deuterated Magic Methyl Group: A Guide to Site-Selective Trideuteromethyl Incorporation and Labeling by Using CD3 Reagents

Joost Steverlynck et al.

Summary: The precise installation of a trideuteromethyl group is gaining attention in medicinal chemistry, with potential pharmacological benefits. This review provides an overview of established methods for site-selective trideuteromethylation and discusses the possibility of introducing CD2H and CDH2 groups, serving as a starting point for advancing trideuteromethylation methodologies for synthetic chemists and offering formation strategies for medicinal chemists in drug preparation.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Review Chemistry, Multidisciplinary

Broadening of horizons in the synthesis of CD3-labeled molecules

Qiao Sun et al.

Summary: Efficient methods for the synthesis of deuterated molecules, particularly CD3-containing ones, have been continuously desired in pharmaceuticals and mechanistic understanding. The recent focus has shifted towards direct incorporating CD3 motifs into molecules, along with the development of various approaches. This review provides an overview of preparation methods for CD3-labeled molecules, ranging from conventional functional group interconversion techniques to catalytic approaches, and includes detailed discussions on reaction mechanisms.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Organic

Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis

Kuan-Lin Chen et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Cyanoamidine Cyclization Approach to Remdesivir's Nucleobase

Rachel R. Knapp et al.

ORGANIC LETTERS (2020)

Article Chemistry, Organic

Total Synthesis of (-)-Clavicipitic Acid via γ,γ-DimethylaIlyltryptophan (DMAT) and Chemoselective C-H Hydroxylation

Francesca Bartoccini et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Concise and Convergent Enantioselective Total Syntheses of (+)-and (-)-Fumimycin

Michele Retini et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Medicinal

Applications of Deuterium in Medicinal Chemistry

Tracey Pirali et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

Article Chemistry, Organic

Asymmetric Total Synthesis and Biological Evaluation of (+)-Cycloclavine

Stephanie R. McCabe et al.

SYNTHESIS-STUTTGART (2019)

Review Chemistry, Multidisciplinary

Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences

Jens Atzrodt et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Catalytic asymmetric formal total syntheses of (+)- and (-)-cycloclavine

Saikat Chaudhuri et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Medicinal

Why Are the Majority of Active Compounds in the CNS Domain Natural Products? A Critical Analysis

Sonali S. Bharate et al.

JOURNAL OF MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Concise Synthesis of (-)-Cycloclavine and (-)-5-epi-Cycloclavine via Asymmetric C-C Activation

Lin Deng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Biotechnology & Applied Microbiology

Ergot Alkaloid Synthesis Capacity of Penicillium camemberti

Samantha J. Fabian et al.

APPLIED AND ENVIRONMENTAL MICROBIOLOGY (2018)

Article Chemistry, Multidisciplinary

Eight-Step Enantioselective Total Synthesis of (-)-Cycloclavine

Stephanie R. McCabe et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Biochemistry & Molecular Biology

Ergot alkaloids: synthetic approaches to lysergic acid and clavine alkaloids

Haichao Liu et al.

NATURAL PRODUCT REPORTS (2017)

Review Chemistry, Multidisciplinary

Recent progress in ergot alkaloid research

Jing-Jing Chen et al.

RSC ADVANCES (2017)

Review Chemistry, Multidisciplinary

Strategies for the Total Synthesis of Clavicipitic Acid

Mamoru Ito et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Clinical Neurology

Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens

Anna Rickli et al.

EUROPEAN NEUROPSYCHOPHARMACOLOGY (2016)

Article Chemistry, Organic

A Modular Formal Total Synthesis of (±)-Cycloclavine

Natalie Netz et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Organic

A simple, modular synthesis of C4-substituted tryptophan derivatives

F. Bartoccini et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Article Biochemistry & Molecular Biology

Dichlorinated and Brominated Rugulovasines, Ergot Alkaloids Produced by Talaromyces wortmannii

Livia Soman de Medeiros et al.

MOLECULES (2015)

Article Chemistry, Organic

Formal Synthesis of (±)-Cycloclavine

Wei Wang et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Organic

Synthesis of (±)-cis-Clavicipitic Acid by a Rh(I)-Catalyzed Intramolecular Imine Reaction

Francesca Bartoccini et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Organic

Formal and total synthesis of (±)-cycloclavine

Nitinkumar D. Jabre et al.

TETRAHEDRON LETTERS (2014)

Review Food Science & Technology

Biosynthetic Pathways of Ergot Alkaloids

Nina Gerhards et al.

TOXINS (2014)

Article Chemistry, Organic

Total Synthesis of Rugulovasine A

Yu-An Zhang et al.

ORGANIC LETTERS (2013)

Article Chemistry, Multidisciplinary

Total Synthesis of (±)-Cycloclavine and (±)-5-epi-Cycloclavine

Filip R. Petronijevic et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Biochemistry & Molecular Biology

Ergot alkaloids: structure diversity, biosynthetic gene clusters and functional proof of biosynthetic genes

Christiane Wallwey et al.

NATURAL PRODUCT REPORTS (2011)

Review Chemistry, Multidisciplinary

Serotonin receptors

David E. Nichols et al.

CHEMICAL REVIEWS (2008)

Review Chemistry, Medicinal

5-HT1A receptor, an old target for new therapeutic agents

Enza Lacivita et al.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2008)

Review Pharmacology & Pharmacy

A role for the 5-HT1A, 5-HT4 and 5-HT6 receptors in learning and memory

Madeleine V. King et al.

TRENDS IN PHARMACOLOGICAL SCIENCES (2008)

Article Chemistry, Applied

Parallel protocol for the selective methylation and alkylation of primary amines

Francesca Cardullo et al.

JOURNAL OF COMBINATORIAL CHEMISTRY (2006)

Article Education, Scientific Disciplines

Ergot and its alkaloids

Paul L. Schiff

AMERICAN JOURNAL OF PHARMACEUTICAL EDUCATION (2006)

Review Pharmacology & Pharmacy

Hallucinogens

DE Nichols

PHARMACOLOGY & THERAPEUTICS (2004)

Review Chemistry, Multidisciplinary

Synthetic preparation of N-methyl-α-amino acids

L Aurelio et al.

CHEMICAL REVIEWS (2004)

Article Multidisciplinary Sciences

Salvinorin A:: A potent naturally occurring nonnitrogenous κ opioid selective agonist

BL Roth et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2002)

Article Chemistry, Multidisciplinary

Applications of vinylogous Mannich reactions.: Total syntheses of the Ergot alkaloids rugulovasines A and B and setoclavine

S Liras et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)