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1 article(s) from Morokuma, Kenji

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

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Graphical Abstract

Figure 1: Artificial glutamate analogs synthesized in an enantiomerically pure form.

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Scheme 1: Our established synthetic route to racemic MC-27 ((rac)-4) [5-7].

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Scheme 2: Resolution of the MC-27 precursor (rac)-7 by a chiral auxiliary.

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Figure 2: Chiral chromatography profiles for the separation of menthyl ester diastereomers 9 and 9*. Conditio...

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Scheme 3: Final elaboration of (2R)-MC-27 (4).

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Figure 3: Superimposed structures of the top 3 stable conformers (76.5% total population) generated by CONFLE...

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Figure 4: Crystallographic analysis of the menthyl ester 10, unequivocally showing the 2R configuration (CCDC...

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Scheme 4: Synthesis of (2S)-MC-27 (4*) from 9*.

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Scheme 5: Construction and chiral resolution of the 5/5/8-ring system towards the TKM-38 enantiomers.

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Figure 5: Structure of Zhan catalyst-1B (14) [14].

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Figure 6: Chiral HPLC profiles for the separation of menthyl ester diastereomers 20* and 20. Conditions: 4.6 ...

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Scheme 6: Final elaboration towards (2R)- and (2S)-TKM-38.

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Figure 7: Superimposed structures of the top 5 stable conformers (89.9% total population) generated by CONFLE...

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Figure 8: Superimposed structures of the top 5 stable conformers (76.8% total population) generated by CONFLE...

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Figure 9: Key interactions that are supposed to control the spatial arrangement of the heterotricycle and the...

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Figure 10: The future synthetic target 22 is expected to show potent neuroactivity.

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Published 24 Feb 2021

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