Orthogonal Syntheses of γ-Carbolinone and Spiro[pyrrolidinone-3,3']indole Derivatives in One Pot through Reaction Telescoping.

The Journal of Organic Chemistry
Souvik GuhaSubhabrata Sen


Herein we report a series of telescoping methodologies for one pot synthesis of biologically relevant γ-carboline derivatives 6 and spiro[pyrrolidinone-3,3']indole 7. Initially the three consecutive steps of cyclopropanation, phthalimide deprotection, and Boc-deprotection have been congregated in a single reaction vessel to afford a ∼1:1 mixture of 6 and 7. Next, careful optimization of the reaction sequence and the conditions generated an orthogonal approach to access compounds 6 and 7 exclusively. Air oxidation of the γ-carbolinones 6 afforded aromatic γ-carbolines 8.


Mar 1, 1986·Journal of Ethnopharmacology·J LeclercqL Angenot
Aug 25, 1971·Journal of the American Chemical Society·W S JohnsonB E McCarry
Jun 1, 1980·Journal of Medicinal Chemistry·C A HarbertB K Koe
Jan 20, 2005·Angewandte Chemie·Mauro MarigoKarl Anker Jørgensen
Jun 22, 1990·Science·S Piettre, C H Heathcock
May 16, 2009·Bioorganic & Medicinal Chemistry Letters·Alexandre V IvachtchenkoSergey E Tkachenko
May 11, 2010·Bioorganic & Medicinal Chemistry·Alexandre BridouxJean-Pierre Henichart
Jul 10, 2010·Journal of the American Chemical Society·Kyle V ButlerAlan P Kozikowski
Aug 22, 2012·Organic Letters·Sangram GoreBurkhard König
Aug 12, 2017·Chemical Society Reviews·Marvin Parasram, Vladimir Gevorgyan
Jun 26, 2018·Chemical Science·Igor D Jurberg, Huw M L Davies
Jul 25, 2018·Chemical Communications : Chem Comm·Tiebo XiaoLei Zhou
Dec 14, 2018·Organic & Biomolecular Chemistry·Łukasz W CiszewskiDorota Gryko
Apr 9, 2019·Chemical Communications : Chem Comm·Feifei He, Rene M Koenigs
Dec 12, 2019·Chemistry : a European Journal·Sripati JanaRene M Koenigs
Jan 31, 2020·Chemistry : a European Journal·Amanda F da SilvaIgor D Jurberg

Related Concepts

Trending Feeds


Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Spatio-Temporal Regulation of DNA Repair

DNA repair is a complex process regulated by several different classes of enzymes, including ligases, endonucleases, and polymerases. This feed focuses on the spatial and temporal regulation that accompanies DNA damage signaling and repair enzymes and processes.

Glut1 Deficiency

Glut1 deficiency, an autosomal dominant, genetic metabolic disorder associated with a deficiency of GLUT1, the protein that transports glucose across the blood brain barrier, is characterized by mental and motor developmental delays and infantile seizures. Follow the latest research on Glut1 deficiency with this feed.

Hereditary Sensory Autonomic Neuropathy

Hereditary Sensory Autonomic Neuropathies are a group of inherited neurodegenerative disorders characterized clinically by loss of sensation and autonomic dysfunction. Here is the latest research on these neuropathies.

Separation Anxiety

Separation anxiety is a type of anxiety disorder that involves excessive distress and anxiety with separation. This may include separation from places or people to which they have a strong emotional connection with. It often affects children more than adults. Here is the latest research on separation anxiety.

Neural Activity: Imaging

Imaging of neural activity in vivo has developed rapidly recently with the advancement of fluorescence microscopy, including new applications using miniaturized microscopes (miniscopes). This feed follows the progress in this growing field.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Related Papers

The Hand
B Chunprapaph, R D Ray
Gastrointestinal Endoscopy
Andrew M Axelrad
Journal of Clinical Rheumatology : Practical Reports on Rheumatic & Musculoskeletal Diseases
Rajiv Ranjan KumarSanjay Jain
International Journal of Psychiatry
J Fort
© 2021 Meta ULC. All rights reserved