A novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition and its application in the synthesis of the cortistatin core.

Tetrahedron Letters
Mingji DaiSamuel J Danishefsky

Abstract

We describe here a novel α,β-unsaturated nitrone-aryne [3+2] cycloaddition. The resulting benzoisoxazolines underwent N-O bond reduction-elimination-electrocyclization sequence to furnish a variety of polysubstituted 2H or 2-alkylated-1-benzo-pyrans. The application of this methodology was further demonstrated in the synthesis of the oxa[3.2.1]octene moiety of cortistatin A.

Citations

Dec 19, 2012·Nature Chemistry·Adam E Goetz, Neil K Garg
Oct 11, 2014·Journal of the American Chemical Society·Jose M MedinaK N Houk
Mar 12, 2011·The Journal of Organic Chemistry·Lichao FangZhen Yang
May 5, 2011·Journal of the American Chemical Society·Jun ShiPhil S Baran
Feb 15, 2012·The Journal of Organic Chemistry·Chun LuRichard C Larock
Sep 3, 2009·Journal of the American Chemical Society·K C NicolaouDavid Y-K Chen
Mar 17, 2011·The Journal of Organic Chemistry·Shuji YamashitaMasahiro Hirama
Jun 10, 2011·Organic Letters·Naoyuki KotokuMotomasa Kobayashi
Jul 19, 2011·Journal of the American Chemical Society·Mark G Nilson, Raymond L Funk
Aug 7, 2012·Organic Letters·Sachin Suresh BhojgudeAkkattu T Biju
Aug 11, 2012·Journal of the American Chemical Society·Sarah M BronnerNeil K Garg
Feb 6, 2016·Natural Product Reports·Yuanyou Qiu, Shuanhu Gao
May 8, 2010·Chemical Communications : Chem Comm·Christian SpiteriJohn E Moses
May 14, 2010·Organic & Biomolecular Chemistry·David Yu-Kai Chen, Chih-Chung Tseng
Jun 17, 2010·Chemical Communications : Chem Comm·James D KirkhamJoseph P A Harrity
Jul 2, 2010·Natural Product Reports·Jonathan C Morris, Andrew J Phillips
Sep 24, 2010·Nature Chemistry·Alec N FlyerAndrew G Myers
Sep 19, 2019·Angewandte Chemie·Daniel B Werz, Akkattu T Biju
Mar 13, 2020·Organic & Biomolecular Chemistry·Satrajit InduKrishna P Kaliappan
May 19, 2020·Organic & Biomolecular Chemistry·Satrajit Indu, Krishna P Kaliappan
Jun 19, 2012·Chemistry : a European Journal·Nicky J Willis, Christopher D Bray
Aug 28, 2015·Chemistry : a European Journal·Liping KuangPauline Chiu
Oct 22, 2009·Angewandte Chemie·Victor J CeeK C Nicolaou
Dec 5, 2008·Journal of the American Chemical Society·Hong Myung LeeMatthew D Shair
Oct 17, 2009·Chemical Reviews·Wenyi Zhao
Jun 15, 2010·The Journal of Organic Chemistry·Tanja Gaich, Phil S Baran
Feb 3, 2009·Accounts of Chemical Research·Ryan A ShenviPhil S Baran
Mar 1, 2011·Journal of the American Chemical Society·Sarah M BronnerNeil K Garg
Oct 12, 2010·Organic Letters·Fangmiao YuHongbin Zhai
Oct 13, 2010·The Journal of Organic Chemistry·Arif Kivrak, Richard C Larock
Mar 2, 2017·The Journal of Organic Chemistry·Takashi IkawaShuji Akai
Sep 29, 2020·The Journal of Organic Chemistry·Eito YoshiokaHideto Miyabe
Sep 12, 2019·The Journal of Organic Chemistry·Avishek GuinAkkattu T Biju

❮ 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.