Prostaglandin Total Synthesis Enabled by the Organocatalytic Dimerization of Succinaldehyde.

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Steven H BennettVarinder K Aggarwal

Abstract

Prostaglandins have been attractive targets in total synthesis for over 50 years, resulting in the development of new synthetic strategies and methodologies that have served the broader chemical community. However, these molecules are not just of academic interest, a number of prostaglandin analogues are used in the clinic, and some are even on the WHO list of essential medicines. In this personal account, we describe our own approach to the family of prostaglandins, which centers around the synthesis of a key enal intermediate, formed from the l-proline catalysed dimerization of succinaldehyde. We highlight the discovery and further optimization of this key reaction, its scale up, and subsequent application to a range of prostaglandins.

References

Nov 12, 1975·Journal of the American Chemical Society·E J Corey, H E Ensley
Oct 3, 1973·Journal of the American Chemical Society·R B WoodwardJ W Whitesell
Sep 24, 1969·Journal of the American Chemical Society·E J CoreyW Huber
Jan 1, 1980·Journal of the Chemical Society. Perkin Transactions 1·C C HowardS M Roberts
Oct 3, 1999·Physiological Reviews·S NarumiyaF Ushikubi
Mar 27, 2001·Annual Review of Pharmacology and Toxicology·R M BreyerM D Breyer
Jan 10, 1997·The Journal of Organic Chemistry·Magnus ErikssonThomas Olsson
Jun 27, 2002·Expert Opinion on Pharmacotherapy·Jess T Whitson
Mar 18, 2005·Chirality·Iva ObadalováJosef Hájícek
Jan 13, 2006·British Journal of Pharmacology·R J Flower
Jun 26, 2007·Chemical Reviews·Saibal DasRené Grée
Jul 1, 2007·Biomolecular NMR Assignments·Robert G MoodyMike P Williamson
Apr 22, 2011·Arteriosclerosis, Thrombosis, and Vascular Biology·Emanuela Ricciotti, Garret A FitzGerald
Aug 25, 2011·Journal of the American Chemical Society·Jessica M Hoover, Shannon S Stahl
Aug 17, 2012·Nature·Graeme CoulthardVarinder K Aggarwal
Jan 16, 2013·Journal of the American Chemical Society·Jessica M HooverShannon S Stahl
Feb 14, 2013·Angewandte Chemie·Yujiro Hayashi, Shigenobu Umemiya
Feb 24, 2017·Organic Letters·Shigenobu UmemiyaYujiro Hayashi
Jul 25, 2017·Organic & Biomolecular Chemistry·Haihui Peng, Fen-Er Chen
Apr 1, 2018·Chemistry : a European Journal·Genki KawauchiYujiro Hayashi
Jul 2, 2020·ACS Central Science·Changcheng JingVarinder K Aggarwal
Dec 23, 2019·Chemical Science·Nariyoshi UmekuboYujiro Hayashi

❮ Previous
Next ❯

Citations

Feb 23, 2021·Accounts of Chemical Research·Yujiro Hayashi
Nov 25, 2020·Organic Letters·Nariyoshi Umekubo, Yujiro Hayashi

❮ 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.