Journal ArticleDOI
A new and short method for the synthesis of 2,4-methanoproline
TLDR
2,4-Methanoproline, a supposed non-proteinogenic anti-feedant, was synthesised in 5 steps starting from allyl benzyl ether 3 in 10% overall yield with an intramolecular nucleophilic substitution as the key step for the formation of the bicyclic skeleton.About:
This article is published in Chemical Communications.The article was published on 2002-01-30. It has received 22 citations till now. The article focuses on the topics: Nucleophilic substitution & Bicyclic molecule.read more
Citations
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Journal ArticleDOI
Palladium-Catalyzed Diastereo- and Enantioselective Wagner−Meerwein Shift: Control of Absolute Stereochemistry in the C−C Bond Migration Event
Barry M. Trost,Jia Xie +1 more
TL;DR: The results demonstrate that, during the C-C bond migration process, the chiral catalysts can control the stereochemistry of both the pi-allylpalladium intermediate and the corresponding migration bond.
Journal ArticleDOI
Structural diversity of bicyclic amino acids
TL;DR: An overview of different classes of bicyclic amino acids is reported, taking into account the strategies to achieve structurally diverse templates, and some implications in medicinal chemistry are also disclosed.
Journal ArticleDOI
Photochemical In-Flow Synthesis of 2,4-Methanopyrrolidines: Pyrrolidine Analogues with Improved Water Solubility and Reduced Lipophilicity
Vadym V. Levterov,Oleg M. Michurin,Petro Borysko,Sergey Zozulya,Iryna V. Sadkova,Andrey A. Tolmachev,Andrey A. Tolmachev,Pavel K. Mykhailiuk,Pavel K. Mykhailiuk +8 more
TL;DR: In spite of a higher molecular weight, 2,4-methanopyrrolidines were shown to have higher solubility in water and lower lipophilicity than pyrrolids, important characteristics of bioactive molecules in drug design.
Journal ArticleDOI
4-Fluoro-2,4-methanoproline.
Anton N. Tkachenko,Dmytro S. Radchenko,Pavel K. Mykhailiuk,Oleksandr O. Grygorenko,Igor V. Komarov +4 more
TL;DR: The first fluorinated analogue of the naturally occurring 2,4-methanoproline, 4-fluoro-2,4 -methanol, has been synthesized in five steps from commercially available methyl 2- fluoroacrylate through a photochemical cyclization as a key step in generating a 2-azabicyclo[2.1.1]hexane skeleton.
Journal ArticleDOI
Synthesis of β-, γ-, δ-, ..., ω-halogenated ketones and aldehydes.
TL;DR: A comparison study of Radical Reactions and Oxidation of Halogenated Alcohols through Synthesis of γ-Halo Ketones and Aldehydes and Nucleophilic Substitution .
References
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Journal ArticleDOI
2,4-Methanoproline (2-carboxy-2,4-methanopyrrolidine) and 2,4-methanoglutamic acid (1-amino-1,3-dicarboxycyclobutane) in seeds of Ateleia herbert smithii Pittier (Leguminosae)
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Synthesis of 6-aza-bicyclo[3,2,1]octan-3-ones via vinylogous imide photochemistry: an approach to the synthesis of the hetisine alkaloids.
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Conformational properties of 2,4-methanoproline (2-carboxy-2,4-methanopyrrolidine) in peptides: determination of preferred peptide bond conformation in aqueous solution by proton Overhauser measurements
Journal ArticleDOI
Total synthesis of cyclobutane amino acids from atelia herbert smithii
Philip F. Hughes,Jon Clardy +1 more
TL;DR: Synthese des proline, acide glutamique et acide pyroglutamique pontes methylene-2,4 and de l'acide amino-1 hydroxymethyl-3 cyclobutanecarboxylique a partir de N-benzoyl chloro-3 alaninate de methyle as mentioned in this paper.
Journal ArticleDOI
Total Synthesis of 2,4-methanaproline
TL;DR: In this article, the synthesis of 2,4-methanoproline was achieved utilizing as the key step an intramolecular [2 + 2] photocycloaddition.