Total synthesis of polyrhacitides A and B by use of an iterative strategy for the stereoselective synthesis of 1,3-polyol arrays

Organic Letters
Helge Menz, Stefan F Kirsch

Abstract

The first total syntheses of polyrhacitides A and B, secondary metabolites from Chinese medicinal ants, were accomplished via an iterative approach to the 1,3-polyol motif. For the construction of all stereogenic centers, the catalytic asymmetric Overman esterification was utilized.

References

Nov 19, 1997·Natural Product Reports·B J Rawlings
Apr 16, 1998·The Journal of Biological Chemistry·J A MackintoshA A Gooley
Jul 18, 2001·Journal of the American Chemical Society·S D Dreher, J L Leighton
Nov 1, 2001·Journal of the American Chemical Society·A B SmithM Schelhaas
Jul 11, 2002·Journal of the American Chemical Society·Svetlana A Burova, Frank E McDonald
Feb 26, 2003·Organic Letters·Peter R AndreanaPeng George Wang
Dec 18, 2003·Chemistry : a European Journal·K C NicolaouParaskevi Giannakakou
May 13, 2004·Chemical Reviews·Alexander Deiters, Stephen F Martin
Sep 25, 2004·Organic Letters·Samir BouzBouz, Janine Cossy
Oct 9, 2004·The Journal of Organic Chemistry·Juan MurgaJ Alberto Marco
Mar 3, 2005·Journal of the American Chemical Society·Stefan F Kirsch, Larry E Overman
Jun 25, 2005·Organic & Biomolecular Chemistry·Ian PatersonDebra J Wallace
Nov 15, 2006·Angewandte Chemie·Bernd Schetter, Rainer Mahrwald
Jan 26, 2007·Journal of the American Chemical Society·K C NicolaouJunichiro Yamaguchi
Feb 3, 2007·Chemical Communications : Chem Comm·Ana B GarciaHerbert Waldmann
Jan 31, 2008·The Journal of Organic Chemistry·Laurent FerriéJanine Cossy
Feb 27, 2008·Journal of Natural Products·Zhi-Hong JiangIsao Kouno
May 21, 2008·Angewandte Chemie·Haruhiko FuwaMakoto Sasaki
Aug 29, 2009·The Journal of Organic Chemistry·Chaitan Khosla
Jun 5, 1998·Angewandte Chemie·Christoph Schneider

❮ Previous
Next ❯

Citations

Mar 3, 2005·Journal of the American Chemical Society·Stefan F Kirsch, Larry E Overman
Jul 13, 2011·Journal of the American Chemical Society·Paul E Gormisky, M Christina White
Jun 9, 2015·Frontiers in Chemistry·Kuan ZhengRan Hong
Dec 15, 2016·Organic & Biomolecular Chemistry·Pradeep KumarNamrata Dwivedi
Dec 18, 2015·Chemical Communications : Chem Comm·Angela BredenkampStefan F Kirsch
Feb 19, 2010·Organic & Biomolecular Chemistry·Timm T Haug, Stefan F Kirsch
Feb 12, 2014·Organic & Biomolecular Chemistry·Gullapalli KumaraswamyRajkumar Banerjee
Dec 2, 2017·Chemistry : a European Journal·Feipeng LiuQinghua Bian
May 29, 2010·The Journal of Organic Chemistry·Rui FuPei-Qiang Huang
Oct 15, 2010·Journal of the American Chemical Society·Jeffrey S CannonLarry E Overman
Jun 30, 2019·Organic Letters·Hui Yang, Wen-Hua Zheng
Dec 10, 2016·Journal of Natural Products·Birakishore PadhiDebendra K Mohapatra
Dec 1, 2017·Organic Letters·G Sudhakar ReddyDebendra K Mohapatra
Apr 18, 2012·Organic Letters·Eduard Hartmann, Martin Oestreich

❮ 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.