Menthyl esterification allows chiral resolution for the synthesis of artificial glutamate analogs

• Kenji Morokuma,
• Shuntaro Tsukamoto,
• Kyosuke Mori,
• Kei Miyako,
• Ryuichi Sakai,
• Raku Irie and
• Masato Oikawa

Beilstein J. Org. Chem. 2021, 17, 540–550, doi:10.3762/bjoc.17.48

• the activity is controlled by the ring C. Keywords: chiral resolution; configurational analysis; glutamate; metathesis; neuroactivity; Introduction The ionotropic glutamate receptor (iGluR) mediates the majority of the excitatory neurotransmission in the mammalian central nervous system (CNS) and

• *) [4]. The structural analysis of the diastereomeric menthyl esters obtained after chiral resolution was conducted based on a combination of NOESY data and conformational calculation in that study [4]. In this study, the configurational analysis of the menthyl ester is reasonably justified by X-ray

• ) [10][11][12]. Since 10 was obtained as crystals, the configurational analysis was thereafter confirmed by single-crystal X-ray analysis, as shown in Figure 4. The conformational differences for 10 between the results of the calculations and the analysis of the NMR data compared to the situation in the

Plakilactones G and H from a marine sponge. Stereochemical determination of highly flexible systems by quantitative NMR-derived interproton distances combined with quantum mechanical calculations of ¹³C chemical shifts

• Simone Di Micco,
• Angela Zampella,
• Maria Valeria D’Auria,
• Carmen Festa,
• Simona De Marino,
• Raffaele Riccio,
• Craig P. Butts and
• Giuseppe Bifulco

Beilstein J. Org. Chem. 2013, 9, 2940–2949, doi:10.3762/bjoc.9.331

• support by the University of Salerno and by Ministero dell'Istruzione, dell'Università e della Ricerca (MIUR), PRIN 2009 “Design, conformational and configurational analysis of novel molecular platforms” is gratefully acknowledged.