Toward the Synthesis of Yuzurimine-Type Alkaloids: Stereoselective Construction of the Heterocyclic Portions of Deoxyyuzurimine and Macrodaphnine

Organic Letters
Ichiro HayakawaAkira Sakakura

Abstract

The heterocyclic portions of yuzurimine-type alkaloids, such as deoxyyuzurimine and macrodaphnine, were synthesized by using a stereoselective hydroboration-oxidation reaction to install the C20 methyl group, the intramolecular Mitsunobu reaction to construct the E-ring portion, and the intramolecular SN2 reaction to construct the F-ring portion as key steps.

References

Mar 7, 2002·Journal of the American Chemical Society·Satoshi YokoshimaTohru Fukuyama
Dec 6, 2002·Organic Letters·Masayuki InoueMasahiro Hirama
Feb 7, 2004·Chemical Communications : Chem Comm·Toshiyuki Kan, Tohru Fukuyama
Jun 29, 2006·Journal of the American Chemical Society·Masatoshi ShibuyaYoshiharu Iwabuchi
Jun 22, 1990·Science·S Piettre, C H Heathcock
Jun 26, 2009·Natural Product Reports·Jun'ichi Kobayashi, Takaaki Kubota
Oct 13, 2011·Angewandte Chemie·Matthias E Weiss, Erick M Carreira
Nov 1, 2011·Organic Letters·Guillaume BélangerFrançois Lévesque
Jul 25, 2013·Nature Chemistry·Zhaoyong LuAng Li
Nov 12, 2013·Planta medica·Haifeng WuXudong Xu
Dec 11, 2013·Journal of the American Chemical Society·Artem Shvartsbart, Amos B Smith
Mar 7, 2014·Natural Product Reports·Baldip KangDarren J Dixon
Mar 11, 2015·Journal of the American Chemical Society·Artem Shvartsbart, Amos B Smith
Jun 23, 2015·Chemical Communications : Chem Comm·Ichiro HayakawaHideo Kigoshi
Jan 15, 2016·Angewandte Chemie·Amit Kumar ChattopadhyayStephen Hanessian
Apr 12, 2016·Angewandte Chemie·Ryosuke YamadaTohru Fukuyama
Feb 17, 2017·Chemical Reviews·Amit Kumar Chattopadhyay, Stephen Hanessian
Sep 29, 2017·Journal of the American Chemical Society·Jian LiAng Li
Nov 9, 2017·Angewandte Chemie·Xiaoming ChenHongbin Zhai
Nov 10, 2017·Journal of the American Chemical Society·Heyao ShiDarren J Dixon
Feb 6, 2018·Journal of the American Chemical Society·Jian LiAng Li
Mar 2, 2018·Journal of the American Chemical Society·Wenhao ZhangAng Li
Apr 26, 2018·Organic & Biomolecular Chemistry·Yusuke KitabayashiSatoshi Yokoshima
Mar 29, 2019·Angewandte Chemie·Bo XuFayang G Qiu
Apr 9, 2019·Angewandte Chemie·Yuye ChenJing Xu
May 11, 2019·Journal of the American Chemical Society·Cedric L HugelshoferRichmond Sarpong

❮ 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.

Related Papers

Journal of Natural Products
Ying-Tong DiXiaojiang Hao
Fortschritte der Chemie organischer Naturstoffe = Progress in the chemistry of organic natural products. Progrès dans la chimie des substances organiques naturelles
E Winterfeldt
© 2021 Meta ULC. All rights reserved