Total synthesis of the cyclopeptide alkaloid paliurine E. insights into macrocyclization by ene--enamide RCM

The Journal of Organic Chemistry
Mathieu ToumiGwilherm Evano

Abstract

The total synthesis of (-)-paliurine E is described in 14 steps and 11% overall yield. The first successful application of ene--enamide ring-closing metathesis for macrocyclization serves as the foundation for this synthesis and allowed for a straightforward installation of the challenging cyclic enamide together with the macrocycle. In the course of these synthetic studies, we also found that very subtle and minor structural modification of the enamide resulted in dramatic and unexpected changes of their reactivity since a primary amide or an aromatic aldehyde can be obtained after reaction with Grubbs' second-generation catalyst. Further insights on the macrocyclization by ene--enamide RCM are also discussed.

References

Jun 22, 2001·Organic Letters·S S KindermanF P Rutjes
Jan 24, 2002·Journal of the American Chemical Society·Taoues Temal-LaïbJieping Zhu
Mar 15, 2002·Organic Letters·Martina WolterStephen L Buchwald
Feb 12, 2005·Organic Letters·Brian R McNaughtonBenjamin L Miller

❮ Previous
Next ❯

Citations

Sep 2, 2009·Organic Letters·Jie Zhou, Jon D Rainier
Jul 9, 2009·Chemical Communications : Chem Comm·Gwilherm EvanoAlexis Coste
May 28, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xufen Yu, Dianqing Sun
Jul 22, 2017·The Journal of Organic Chemistry·Kohei TakamotoMitsuhiro Arisawa
Feb 20, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guorui CaoDawei Teng
Dec 17, 2014·Organic & Biomolecular Chemistry·Pauline PetiotAlexandre Gagnon
May 28, 2014·Chemistry : a European Journal·Nicolas GigantIsabelle Gillaizeau
Dec 17, 2008·Organic & Biomolecular Chemistry·David R Carbery
Jul 16, 2011·Angewandte Chemie·Gang Liu, Daniel Romo
Jul 1, 2011·Journal of the American Chemical Society·Ji-Shen ZhengLei Liu
Nov 5, 2014·The Journal of Organic Chemistry·Andrew D WadsworthMargaret A Brimble
Jan 27, 2019·The Journal of Organic Chemistry·Alessandro ManfrinKristopher McNeill
Sep 6, 2014·Organic Letters·Heather J JohnstonAlison N Hulme
Aug 28, 2021·RSC Medicinal Chemistry·Clément Bechtler, Christina Lamers

❮ 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.