Enantioselective synthesis of (-)-paeonilide

Chemical Communications : Chem Comm
Klaus Harrar, Oliver Reiser

Abstract

The first enantioselective synthesis of (-)-paeonilide is reported. Starting from inexpensive furan-3-carboxylic acid the targeted monoterpene was obtained in 12 steps via an asymmetric cyclopropanation-lactonization cascade and a stereoselective side chain insertion at an acetal-like position.

References

Sep 19, 2000·Bioscience, Biotechnology, and Biochemistry·X D LiuW J Coumans
May 12, 2001·Organic Letters·C Böhm, O Reiser
Dec 31, 2002·Chemistry : a European Journal·Rakeshwar B ChhorOliver Reiser
Apr 10, 2003·Chemical Reviews·Hans-Ulrich Reissig, Reinhold Zimmer
Feb 3, 2004·Angewandte Chemie·Thomas P BradyEmmanuel A Theodorakis
Jun 9, 2005·Current Opinion in Chemical Biology·Michael Seitz, Oliver Reiser
Nov 18, 2005·Organic Letters·Roland WeisserOliver Reiser
Jun 2, 2006·Organic Letters·Chenying WangHongbin Zhang
Mar 6, 2007·Organic Letters·Shrutisagar Dattatraya HaveliSrinivasan Chandrasekaran
Apr 7, 2007·The Journal of Organic Chemistry·Yuguo DuRobert J Linhardt
Jul 20, 2007·Angewandte Chemie·Srinivas KalidindiOliver Reiser
Dec 20, 2008·Journal of Pharmaceutical and Biomedical Analysis·Lu ChenDanni Zhu
Mar 2, 2011·Organic & Biomolecular Chemistry·Martin SchanderlOliver Reiser

❮ Previous
Next ❯

Citations

Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Jun 24, 2017·Chemical Reviews·Bin MaoBen L Feringa
Mar 17, 2015·Angewandte Chemie·Liang WangPingping Tang
Apr 29, 2014·Angewandte Chemie·Tobias F SchneiderDaniel B Werz
Sep 13, 2012·Organic Letters·Fedor Romanov-MichailidisAlexandre Alexakis
Jul 21, 2020·Journal of the American Chemical Society·Xinpei CaiMingji Dai
Aug 19, 2021·Journal of the American Chemical Society·Anna E VartanovaIgor V Alabugin

❮ 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.