Asymmetric total synthesis of Apocynaceae hydrocarbazole alkaloids (+)-deethylibophyllidine and (+)-limaspermidine

Journal of the American Chemical Society
Ji-Yuan DuChun-An Fan

Abstract

An unprecedented asymmetric catalytic tandem aminolysis/aza-Michael addition reaction of spirocyclic para-dienoneimides has been designed and developed through organocatalytic enantioselective desymmetrization. A unified strategy based on this key tandem methodology has been divergently explored for the asymmetric total synthesis of two natural Apocynaceae alkaloids, (+)-deethylibophyllidine and (+)-limaspermidine. The present studies not only enrich the tandem reaction design concerning the asymmetric catalytic assembly of a chiral all-carbon quaternary stereocenter contained in the densely functionalized hydrocarbazole synthons but also manifest the potential for the application of the asymmetric catalysis based on the para-dienone chemistry in asymmetric synthesis of natural products.

References

Jan 5, 2002·Chemical Reviews·Josep Bonjoch, Daniel Solé
Jan 10, 2002·Journal of the American Chemical Society·Rosalinde ImbosBen L Feringa
Oct 31, 2002·Angewandte Chemie·Jens Christoffers, Alexander Mann
Jul 23, 2003·Current Medicinal Chemistry·Antonio Ramírez, Silvina García-Rubio
Jan 16, 2004·Proceedings of the National Academy of Sciences of the United States of America·Christopher J Douglas, Larry E Overman
Apr 2, 2004·Nature Reviews. Cancer·Mary Ann Jordan, Leslie Wilson
Feb 22, 2005·Chemical Reviews·Eduardo García-UrdialesVicente Gotor
Nov 17, 2005·Journal of the American Chemical Society·Yujiro HayashiMitsuru Shoji
Feb 24, 2006·Angewandte Chemie·Mark S Taylor, Eric N Jacobsen
Mar 4, 2006·Chemistry : a European Journal·Stephen J Connon
Oct 16, 2007·Chemistry, an Asian Journal·Justin T Mohr, Brian M Stoltz
Dec 13, 2007·Chemical Reviews·Iuliana AtodireseiCarsten Bolm
Dec 13, 2007·Chemical Reviews·Abigail G Doyle, Eric N Jacobsen
Dec 14, 2007·Journal of the American Chemical Society·Guillaume Barbe, André B Charette
Dec 18, 2007·Journal of the American Chemical Society·Ngoc T VoMatthew J Gaunt
Feb 29, 2008·Journal of the American Chemical Society·Amy B DounayAaron D Wrobleski
May 29, 2008·Chemical Communications : Chem Comm·Stephen J Connon
Aug 30, 2008·Journal of the American Chemical Society·Le LiDaniel Seidel
Apr 25, 2009·Journal of the American Chemical Society·Jorge García-FortanetStephen L Buchwald
May 8, 2009·Chemical Society Reviews·Zhiguo Zhang, Peter R Schreiner
Jul 9, 2009·Journal of the American Chemical Society·Barbara WeinerBen L Feringa
Sep 4, 2009·Journal of the American Chemical Society·Spencer B JonesDavid W C MacMillan
Oct 3, 2009·Chemistry : a European Journal·Dieter EndersJens X Liebich
Mar 9, 2010·Journal of the American Chemical Society·Qing GuShu-Li You
Aug 25, 2010·Chemical Communications : Chem Comm·Christine Hawner, Alexandre Alexakis
Dec 2, 2010·Chemical Communications : Chem Comm·Zhi-Hua ChenFu-Min Zhang
Mar 2, 2011·Chemical Communications : Chem Comm·Jaya Prakash Das, Ilan Marek
Mar 15, 2011·Chemical Society Reviews·R Ian StorerLyn H Jones
Apr 16, 2011·Accounts of Chemical Research·Dan ZhangYong Qin
Apr 30, 2011·Chemical Reviews·Eduardo García-UrdialesVicente Gotor
May 19, 2011·Chemistry : a European Journal·José AlemánKarl Anker Jørgensen
Jun 18, 2011·The Journal of Organic Chemistry·Rui-jiong LuMing Yan
Jul 7, 2011·Accounts of Chemical Research·Baomin Wang, Yong Qiang Tu
Jul 15, 2011·Nature·Spencer B JonesDavid W C MacMillan
Sep 29, 2011·Organic & Biomolecular Chemistry·Rodolfo Tello-AburtoAndrew M Harned
Feb 16, 2012·The Journal of Organic Chemistry·Kimiaka C GuérardSylvain Canesi

❮ Previous
Next ❯

Citations

Dec 1, 2015·The Journal of Organic Chemistry·Zhuang ChenYanxing Jia
Aug 12, 2016·Journal of the American Chemical Society·Kolby L White, Mohammad Movassaghi
Apr 28, 2017·Journal of the American Chemical Society·Xian-He ZhaoChun-An Fan
May 27, 2017·Journal of the American Chemical Society·Huan XuQi-Lin Zhou
Sep 2, 2017·Angewandte Chemie·Taek KangMohammad Movassaghi
Jun 19, 2018·Organic & Biomolecular Chemistry·Marta GuerolaCarlos Del Pozo
Apr 7, 2018·Chemistry : a European Journal·Yanshi WangYongxiang Liu
Sep 8, 2015·Chemistry, an Asian Journal·Yong HuangEric Meggers
Jun 28, 2016·Chemical Society Reviews·A BorissovD J Dixon
Sep 1, 2015·Angewandte Chemie·Yuanyuan YuLiansuo Zu
Oct 20, 2020·Natural Product Reports·Franziska Reuß, Philipp Heretsch
Dec 14, 2019·The Journal of Organic Chemistry·Yi-Guo ZhouXiao-Shui Peng
Dec 9, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Nengzhong Wang, Xuefeng Jiang
Jun 20, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Anandarao MunakalaRambabu Chegondi
Mar 9, 2018·Chemical Reviews·Lei LiYanxing Jia
Aug 21, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·María Sánchez-RosellóCarlos Del Pozo
Sep 25, 2021·Chemical Communications : Chem Comm·Shi TangJian Wang
Oct 8, 2021·Chemical Communications : Chem Comm·Haizhen LiWei-Dong Z Li

❮ 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.