scholarly journals Short Synthesis of Idraparinux by Applying a 2-O -Methyl-4,6-O -arylmethylene Thioidoside as a 1,2-trans -α-Selective Glycosyl Donor

2018 ◽  
Vol 2018 (48) ◽  
pp. 6901-6912
Author(s):  
Fruzsina Demeter ◽  
Fanni Veres ◽  
Mihály Herczeg ◽  
Anikó Borbás
Keyword(s):  
Glycosyl Donor ◽  
Short Synthesis

A Short Synthesis of (+)-Brefeldin C via Enantioselective Radical Hydroalkynylation

2019 ◽  
Author(s):  
Lars Gnägi ◽  
Severin Vital Martz ◽  
Daniel Meyer ◽  
Robin Marc Schärer ◽  
Philippe Renaud
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Oxidation State ◽  
Single Step ◽  
Radical Process ◽  
Target Molecule ◽  
Short Synthesis ◽  
The One

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>

A Short Synthesis of the Plant Alkaloid 4-Methyl-2,6-naphthyridine

2019 ◽  
Vol 16 (12) ◽  
pp. 931-934 ◽  
Author(s):  
Alexandra Kamlah ◽  
Franz Bracher
Keyword(s):  
Pyridine Ring ◽  
Cross Coupling ◽  
Antirrhinum Majus ◽  
New Synthesis ◽  
Short Synthesis ◽  
Regioselective Oxidation ◽  
Key Steps

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.

scholarly journals A One-Pot Approach to Novel Pyridazine C-Nucleosides

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2341
Author(s):  
Flavio Cermola ◽  
Serena Vella ◽  
Marina DellaGreca ◽  
Angela Tuzi ◽  
Maria Rosaria Iesce
Keyword(s):  
Organic Chemistry ◽  
Research Field ◽  
Modified Nucleosides ◽  
Protecting Groups ◽  
Coupling Reactions ◽  
One Pot ◽  
Pharmacological Interest ◽  
Classical Methodology ◽  
Glycosyl Donor ◽  
Neutral Conditions

The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new C-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine C-nucleosides starting with 2- and 3-(ribofuranosyl)furans. It is based on singlet oxygen [4+2] cycloaddition followed by reduction and hydrazine cyclization under neutral conditions. The mild three-step one-pot procedure leads stereoselectively to novel pyridazine C-nucleosides of pharmacological interest. The use of acetyls as protecting groups provides an elegant direct route to a deprotected new pyridazine C-nucleoside.

scholarly journals Cold-Active β-Galactosidases: Insight into Cold Adaption Mechanisms and Biotechnological Exploitation

Marine Drugs ◽  
2021 ◽  
Vol 19 (1) ◽  
pp. 43
Author(s):  
Marco Mangiagalli ◽  
Marina Lotti
Keyword(s):  
Low Temperature ◽  
Molecular Mechanisms ◽  
Building Blocks ◽  
Cold Active ◽  
Cold Adaption ◽  
Glycosyl Donor ◽  
Pharmaceutical Industries ◽  
Biotechnological Processes ◽  
Hydrolysis Of ◽  
Insight Into

β-galactosidases (EC 3.2.1.23) catalyze the hydrolysis of β-galactosidic bonds in oligosaccharides and, under certain conditions, transfer a sugar moiety from a glycosyl donor to an acceptor. Cold-active β-galactosidases are identified in microorganisms endemic to permanently low-temperature environments. While mesophilic β-galactosidases are broadly studied and employed for biotechnological purposes, the cold-active enzymes are still scarcely explored, although they may prove very useful in biotechnological processes at low temperature. This review covers several issues related to cold-active β-galactosidases, including their classification, structure and molecular mechanisms of cold adaptation. Moreover, their applications are discussed, focusing on the production of lactose-free dairy products as well as on the valorization of cheese whey and the synthesis of glycosyl building blocks for the food, cosmetic and pharmaceutical industries.

ChemInform Abstract: A Short Synthesis of (.+-.)-Ricciocarpin a Using Intramolecular Reductive Michael Reaction.

ChemInform ◽  
2010 ◽  
Vol 29 (18) ◽  
pp. no-no
Author(s):  
K. TAKEDA ◽  
N. OHKAWA ◽  
K. HORI ◽  
T. KOIZUMI ◽  
E. YOSHII
Keyword(s):  
Michael Reaction ◽  
Short Synthesis

A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group

1996 ◽  
Vol 37 (11) ◽  
pp. 1885-1888 ◽  
Author(s):  
A.J. Bloodworth ◽  
Brian D Bothwell ◽  
Andrew N Collins ◽  
Nicola L Maidwell
Keyword(s):  
Naturally Occurring ◽  
Short Synthesis

ChemInform Abstract: A Short Synthesis of 3,6-Disubstituted N-2-Thienyl/Aryl-indoles.

ChemInform ◽  
2010 ◽  
Vol 41 (10) ◽  
Author(s):  
Hanumant B. Borate ◽  
Sangmeshwer P. Sawargave ◽  
Suleman R. Maujan
Keyword(s):  
Short Synthesis

Phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside: a glycosyl donor

2007 ◽  
Vol 63 (9) ◽  
pp. o3772-o3772
Author(s):  
Yow-Fu Tsai ◽  
Jen-Ta Yang ◽  
Jhy-Der Chen ◽  
Chia-Her Lin
Keyword(s):  
Glycosyl Donor
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