Synthesis of Carbazole Alkaloids by Ring-Closing Metathesis and Ring Rearrangement-Aromatization

Angewandte Chemie
Kalyan DharaJyotirmayee Dash

Abstract

Aprocess for the assembly of carbazole alkaloids has been developed on the basis of ring-closing metathesis (RCM) and ringrearrangement-aromatization (RRA) as the key steps. This method is based on allyl Grignard addition to isatin derivatives to provide smooth access to 2,2-diallyl 3-oxindole derivatives through a 1,2-allyl shift. The diallyl derivatives were used as RCM precursors to afford a novel class of spirocyclopentene-3-oxindole derivatives, which underwent a novel RRA reaction to afford carbazole derivatives. The synthetic sequence to carbazoles was shortened by combining the RCM and RRA steps in an orthogonal tandem catalytic process. The utility of this methodology was further demonstrated by the straightforward synthesis of carbazole alkaloids, including amukonal derivative, girinimbilol, heptaphylline, and bis(2-hydroxy-3-methylcarbazole).

References

Feb 1, 1995·Phytochemistry·A ChakrabortyP Bhattacharyya
Feb 15, 2001·Accounts of Chemical Research·T M Trnka, R H Grubbs
May 10, 2002·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Stefan Tasler, Gerhard Bringmann
Mar 8, 2003·Planta medica·Arunrat SunthitikawinsakulSasarose Rochanaruangrai
May 13, 2004·Chemical Reviews·Alexander Deiters, Stephen F Martin
Mar 10, 2005·Chemical Reviews·Julia-Christina WasilkeGuillermo C Bazan
Oct 20, 2005·Journal of the American Chemical Society·W C Peter TsangStephen L Buchwald
Dec 6, 2005·The Journal of Organic Chemistry·Stephen C PellyCharles B de Koning
Jan 5, 2006·Journal of the American Chemical Society·Byung Gyu Kim, Marc L Snapper
Feb 14, 2006·The Journal of Organic Chemistry·Jean-Philippe LeclercKeith Fagnou
Feb 14, 2006·Angewandte Chemie·Samuel BelignySiegfried Blechert
Mar 21, 2006·Angewandte Chemie·Timothy J DonohoeMatilda Bingham
Aug 26, 2006·The Journal of Organic Chemistry·M Lluïsa BennasarDavinia García-Díaz
Dec 2, 2006·The Journal of Organic Chemistry·Robin B Bedford, Michael Betham
Dec 25, 2007·Organic Letters·Timothy J DonohoePanayiotis A Procopiou
Feb 21, 2008·Angewandte Chemie·Jia-Rong ChenWen-Jing Xiao
Apr 3, 2008·Chemistry : a European Journal·Timothy J DonohoePanayiotis A Procopiou
May 30, 2008·Chemistry : a European Journal·Bernd Schmidt, Anne Biernat
Nov 13, 2008·Journal of the American Chemical Society·James A Jordan-HoreMatthew J Gaunt
Jul 22, 2009·Chemical Reviews·Willem A L van Otterlo, Charles B de Koning
Aug 15, 2009·Angewandte Chemie·Florian Monnier, Marc Taillefer
Aug 7, 2010·The Journal of Organic Chemistry·Nina DeppermannWolfgang Maison
Sep 2, 2010·The Journal of Organic Chemistry·Victoria HelanDaniel Grant
Jun 7, 2011·European Journal of Medicinal Chemistry·Tula ThongthoomChavi Yenjai
Apr 7, 2012·Chemical Reviews·Arndt W SchmidtHans-Joachim Knölker
Apr 10, 2012·Journal of Natural Products·Wisanu ManeeratSurat Laphookhieo
Sep 4, 2012·The Journal of Organic Chemistry·Kalyan DharaJyotirmayee Dash
Sep 7, 2012·Chemical Reviews·Girija S Singh, Zelalem Y Desta
Jan 12, 2013·Chemical Reviews·Anton V GulevichVladimir Gevorgyan

❮ Previous
Next ❯

Citations

Jun 15, 2017·The Journal of Organic Chemistry·Uttam K MishraS S V Ramasastry
Mar 14, 2018·Chemistry : a European Journal·Hortense LauwickMathieu Achard
Nov 30, 2018·Chemical Communications : Chem Comm·Puja SahaJyotirmayee Dash
Nov 9, 2017·Angewandte Chemie·Xiaoming ChenHongbin Zhai
Apr 10, 2019·Organic & Biomolecular Chemistry·Andrey G LvovValerii Z Shirinian
Jan 24, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xue YanHua Zhang
Oct 13, 2017·Chemistry : a European Journal·Christian BrüttingHans-Joachim Knölker
Mar 6, 2018·Bioorganic & Medicinal Chemistry Letters·Makoto SakoShinobu Takizawa
Dec 10, 2016·Organic Letters·Yi-Wei HuangQi-Xiang Guo
Dec 17, 2016·Organic Letters·B Narendraprasad Reddy, Chepuri V Ramana
Nov 9, 2021·Organic & Biomolecular Chemistry·Tirtha Mandal, Jyotirmayee Dash

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

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.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

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.

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.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

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.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.