77422-38-9Relevant academic research and scientific papers
Photochemical In-Flow Synthesis of 2,4-Methanopyrrolidines: Pyrrolidine Analogues with Improved Water Solubility and Reduced Lipophilicity
Levterov, Vadym V.,Michurin, Oleg,Borysko, Petro O.,Zozulya, Sergey,Sadkova, Iryna V.,Tolmachev, Andrey A.,Mykhailiuk, Pavel K.
, p. 14350 - 14361 (2018/11/23)
A practical synthesis of 2,4-methanopyrrolidines was elaborated. The key synthetic step was an intramolecular photochemical [2 + 2]-cycloaddition of an acrylic acid derivative in flow. In spite of a higher molecular weight, 2,4-methanopyrrolidines were shown to have higher solubility in water and lower lipophilicity than pyrrolidines, important characteristics of bioactive molecules in drug design.
Efficient preparation of 2,4-methanoproline
Varnes, Jeffrey G.,Lehr, G. Scott,Moore, Gary L.,Hulsizer, James M.,Albert, Jeffrey S.
scheme or table, p. 3756 - 3758 (2010/08/20)
Using a modification of the route described by Clardy and Hughes et al., 2,4-methanoproline hydrochloride (1) was prepared in four steps and 70% overall yield from DL-serine methyl ester.
Total Synthesis of Cyclobutane Amino Acids from Atelia herbert smithii
Hughes, Philip,Clardy, Jon
, p. 4793 - 4797 (2007/10/02)
The syntheses of two amino acids from the seeds of the legume Atelia herbert smithii, 2,4-methanoproline and 2,4-methanoglutamic acid, are described.The synthesis of third amino acid, cis-1-amino-3-(hydroxymethyl)cyclobutanecarboxylic acid and subsequent
SYNTHESIS OF 2,4-METHANOPROLINE
Hughes, Philip,Martin, Michael,Clardy, Jon
, p. 4579 - 4580 (2007/10/02)
An efficient synthesis of 2,4-methanoproline from serine is described.The cyclobutane is formed by a sensitized intramolecular photoaddition.
