Organocatalytic, Asymmetric Total Synthesis of (-)-Haliclonin A

Angewandte Chemie
Lian-Dong GuoPei-Qiang Huang

Abstract

The first total synthesis of the alkaloid (-)-haliclonin A is reported. The asymmetric synthesis relied on a novel organocatalytic asymmetric conjugate addition of nitromethane with 3-alkenyl cyclohex-2-enone to set the stereochemistry of the all-carbon quaternary stereogenic center. The synthesis also features a Pd-promoted cyclization to form the 3-azabicyclo[3,3,1]nonane core, a SmI2 -mediated intermolecular reductive coupling of enone with aldehyde to form the requisite secondary chiral alcohol, ring-closing alkene and alkyne metathesis reactions to build the two aza-macrocyclic ring systems, and an unprecedented direct transformation of enol into enone.

References

May 7, 2005·Chemical Communications : Chem Comm·Alois Furstner, Paul W Davies
Jul 9, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Oct 14, 2005·Journal of the American Chemical Society·Arnab K ChatterjeeRobert H Grubbs
Oct 26, 2005·Chemical Communications : Chem Comm·Claire E T MitchellSteven V Ley
Mar 28, 2006·Angewandte Chemie·Neil K GargLarry E Overman
Oct 3, 2006·Angewandte Chemie·K C NicolaouDavid J Edmonds
Sep 14, 2007·Journal of the American Chemical Society·Michael H BeckerLarry E Overman
Mar 20, 2009·Organic Letters·Kyoung Hwa JangJongheon Shin
Aug 12, 2010·Journal of the American Chemical Society·Johannes HeppekausenAlois Fürstner
Apr 28, 2012·Journal of the American Chemical Society·Ming BianAng Li
Dec 12, 2012·The Journal of Organic Chemistry·Hao-Hua HuoPei-Qiang Huang
Dec 12, 2012·Chemistry : a European Journal·Shi-Peng LuoPei-Qiang Huang
Jan 29, 2013·Angewandte Chemie·Alois Fürstner
Jan 15, 2014·Chemical Communications : Chem Comm·Qi-Long PengPei-Qiang Huang
Apr 25, 2014·Chemical Reviews·Michal SzostakDavid J Procter
Dec 17, 2014·Nature·Kyle W Quasdorf, Larry E Overman
Jan 22, 2015·Chemical Communications : Chem Comm·Pei-Qiang HuangAi-E Wang
Feb 5, 2015·Angewandte Chemie·Michael Fuchs, Alois Fürstner
Mar 23, 2015·Angewandte Chemie·Michael Fuchs, Alois Fürstner
Jul 3, 1998·Angewandte Chemie·Alois Fürstner, Günter Seidel

❮ Previous
Next ❯

Citations

Apr 27, 2016·Chemistry : a European Journal·Ya DuWei Zhang
Nov 7, 2018·Chemistry : a European Journal·Bernhard WölflAlois Fürstner
Nov 7, 2018·Chemistry : a European Journal·Guillaume MataAlois Fürstner
Oct 23, 2018·Chemistry : a European Journal·Henrike Ehrhorn, Matthias Tamm
Sep 27, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Hui Geng, Pei-Qiang Huang
Jan 18, 2018·Natural Product Reports·John W BluntMichèle R Prinsep
Nov 16, 2019·Beilstein Journal of Organic Chemistry·Celine BittnerMatthias Tamm
Sep 17, 2019·Natural Product Reports·Bichu Cheng, Julius Reyes
Aug 22, 2020·Angewandte Chemie·Alois FürstnerChristophe Copéret
Oct 13, 2020·Chemistry : a European Journal·Xiu-Ning HuPei-Qiang Huang
Feb 10, 2021·Angewandte Chemie·Yuan JinSatoshi Yokoshima
Jun 17, 2020·Journal of the American Chemical Society·Zhanchao Meng, Alois Fürstner
Sep 10, 2019·The Journal of Organic Chemistry·Qing ZhangYong-Qiang Tu
May 29, 2020·Journal of the American Chemical Society·Julius HillenbrandAlois Fürstner
Dec 22, 2017·The Journal of Organic Chemistry·Zhanchao MengAlois Fürstner
May 30, 2019·Journal of the American Chemical Society·Rulin MaM Christina White
Sep 15, 2021·Journal of the American Chemical Society·Alois Fürstner

❮ 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.