A photoinduced cyclization cascade-total synthesis of (-)-leuconoxine

Chemistry : a European Journal
Magnus Pfaffenbach, Tanja Gaich

Abstract

A protecting-group-free and enantioselective total synthesis of the monoterpenoid indole alkaloid (-)-leuconoxine was accomplished. The key step comprises a novel photoinduced domino macrocyclization/transannular cyclization involving the Witkop cyclization, for which additional mechanistic evidence is provided. This process furnishes a diaza[5.5.6.6]fenestrane skeleton, which is a hitherto unprecedented structure element.

References

Jul 29, 2006·Natural Product Reports·Sarah E O'Connor, Justin J Maresh
Dec 15, 2006·Chemical Reviews·Reinhart Keese
Mar 28, 2007·Angewandte Chemie·Chaomin LiSamuel J Danishefsky
May 29, 2007·Chemical Reviews·Maurizio FagnoniAngelo Albini
Jul 5, 2007·Journal of Natural Products·Siew-Huah LimToh-Seok Kam
Mar 14, 2008·Organic Letters·Jakob MagolanMichael A Kerr
Jan 15, 2009·Journal of the American Chemical Society·Tanja Gaich, Johann Mulzer
Jul 18, 2009·Planta medica·Tao FengXiao-Dong Luo
Dec 17, 2009·Organic Letters·Tanja Gaich, Johann Mulzer
Jan 1, 2010·Journal of Natural Products·Tao FengXiao-Dong Luo
Jan 9, 2010·Journal of the American Chemical Society·Rie NakajimaTohru Fukuyama
Jun 1, 2009·Nature Chemistry·Ian S Young, Phil S Baran
Jun 15, 2011·Journal of Natural Products·Nattha IngavatPrasat Kittakoop
Apr 20, 2012·Organic Letters·Yusuke IwamaHidetoshi Tokuyama
Sep 20, 2012·Chemical Society Reviews·Davide RavelliAngelo Albini
Mar 8, 2013·Natural Product Reports·Minoru IshikuraSatoshi Hibino
May 8, 2013·Journal of Natural Products·Chew-Yan GanToh-Seok Kam
Jun 5, 2013·Chemistry : a European Journal·Yusuke IwamaHidetoshi Tokuyama
Nov 28, 2013·Angewandte Chemie·Aicha BoudharJean Suffert
Dec 11, 2013·Angewandte Chemie·Philipp J GritschTanja Gaich
Dec 18, 2013·Journal of the American Chemical Society·Zhengren XuJieping Zhu
Feb 22, 2014·Organic Letters·Zhe LvGuangxin Liang

❮ Previous
Next ❯

Citations

Apr 14, 2016·Chemical Reviews·Davide RavelliMaurizio Fagnoni
Apr 3, 2016·Chemistry : a European Journal·Magnus PfaffenbachTanja Gaich
Oct 8, 2015·Chemistry : a European Journal·Magnus Pfaffenbach, Tanja Gaich
Jul 22, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·José Tiago M CorreiaMárcio W Paixão
Sep 20, 2019·The Journal of Organic Chemistry·Jing Zhang, Fu-She Han

❮ 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.

Related Papers

Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
T Naito
© 2021 Meta ULC. All rights reserved