Synthesis of angiolam A

Organic Letters
Marc Timo Gieseler, Markus Kalesse

Abstract

The first total synthesis of angiolam A has been accomplished in 18 steps. Key steps include vinylogous Mukaiyama aldol reactions of aldehyde-derived dienol ethers, conjugate reduction of the resulting double bond followed by diastereoselective protonation and the Witzeman protocol for macrolactamization. Comparison of the optical rotation of the synthesized material with the isolation data established that the absolute configuration of angiolam A is opposite from the proposed structure.

References

Jun 9, 2005·Angewandte Chemie·Scott E DenmarkGregory L Beutner
Sep 25, 2007·Organic Letters·Lars V Heumann, Gary E Keck
Dec 7, 2007·Organic Letters·Serkan SimsekMarkus Kalesse
Dec 7, 2007·Organic Letters·James A Marshall, Patrick M Eidam
Jan 1, 2008·Chemistry : a European Journal·Gunnar EhrlichMarkus Kalesse
Mar 19, 2009·Angewandte Chemie·Noah Z BurnsReinhard W Hoffmann
Sep 30, 2010·Angewandte Chemie·Anastasie Kena DibaMarkus Kalesse
Mar 26, 2011·Chemical Reviews·Giovanni CasiraghiFranca Zanardi
Apr 9, 2011·Organic Letters·Marc T Gieseler, Markus Kalesse
Mar 10, 2012·Organic Letters·Gerrit Symkenberg, Markus Kalesse

❮ Previous
Next ❯

Citations

Apr 19, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Paul J FischerVictor G Young
Jan 20, 2015·Chemical Communications : Chem Comm·Kai FuXiaoming Feng
Mar 7, 2014·Natural Product Reports·Markus KalesseHai-Hua Lu
May 21, 2014·Natural Product Reports·Till F SchäberleGabriele M König
Nov 24, 2017·Chemistry : a European Journal·Frank SurupMarkus Kalesse
Jun 8, 2019·Chemistry : a European Journal·Daniel Lücke, Markus Kalesse
Feb 19, 2020·Chemistry : a European Journal·Yannick LinneMarkus Kalesse
May 5, 2020·Beilstein Journal of Organic Chemistry·Jan Geldsetzer, Markus Kalesse
Jan 16, 2021·Angewandte Chemie·Yannick LinneMarkus Kalesse
Mar 12, 2019·The Journal of Organic Chemistry·Xianying GaoYangjie Wu
Jul 14, 2018·Organic Letters·Daniel LückeMarkus Kalesse
Aug 9, 2017·The Journal of Organic Chemistry·Qiang LiuYun He
Aug 16, 2017·Organic Letters·Caroline Poock, Markus Kalesse
Nov 6, 2021·Organic Letters·Alina EggertMarkus Kalesse

❮ 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.

© 2021 Meta ULC. All rights reserved