Construction of trans-2,6-Disubstituted Piperidine Skeleton and Its Application to the Total Synthesis of (−)-Myrtine and trans-Piperidine-Type Poison-Frog Alkaloids

Takuya Okada; Kenta Eguchi; Fumiaki Hasegawa; Mir Mohd Ikhlaq; Takahiro Yoshikawa; Naoki Toyooka

doi:10.1021/acs.joc.4c02976

Construction of trans-2,6-Disubstituted Piperidine Skeleton and Its Application to the Total Synthesis of (−)-Myrtine and trans-Piperidine-Type Poison-Frog Alkaloids

Takuya Okada^*, Kenta Eguchi, Fumiaki Hasegawa, Mir Mohd Ikhlaq, Takahiro Yoshikawa, Naoki Toyooka

^*Corresponding author for this work

Life Sciences and Bioengineering

Research output: Contribution to journal › Article › peer-review

Abstract

We have succeeded in constructing a trans-2,6-disubstituted piperidine (trans-2,6-DP) skeleton by treatment of allylsilane derivative 2 with TMSOTf. Our designed trans-2,6-DP 1 has oxygen functional groups at the 2- and 6-positions and an exo-methylene moiety at the 4-position and is expected to be applied not only to the synthesis of various natural products but also as an excellent chiral building block with pseudo-symmetry. To demonstrate the versatility of 1, the total synthesis of (−)-myrtin and trans-piperidine-type poison-frog alkaloid 213A and 213B was accomplished.

Original language	English
Pages (from-to)	2749-2759
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	90
Issue number	7
DOIs	https://doi.org/10.1021/acs.joc.4c02976
State	Published - 2025/02/21

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Organic Chemistry

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title = "Construction of trans-2,6-Disubstituted Piperidine Skeleton and Its Application to the Total Synthesis of (−)-Myrtine and trans-Piperidine-Type Poison-Frog Alkaloids",

abstract = "We have succeeded in constructing a trans-2,6-disubstituted piperidine (trans-2,6-DP) skeleton by treatment of allylsilane derivative 2 with TMSOTf. Our designed trans-2,6-DP 1 has oxygen functional groups at the 2- and 6-positions and an exo-methylene moiety at the 4-position and is expected to be applied not only to the synthesis of various natural products but also as an excellent chiral building block with pseudo-symmetry. To demonstrate the versatility of 1, the total synthesis of (−)-myrtin and trans-piperidine-type poison-frog alkaloid 213A and 213B was accomplished.",

author = "Takuya Okada and Kenta Eguchi and Fumiaki Hasegawa and Ikhlaq, {Mir Mohd} and Takahiro Yoshikawa and Naoki Toyooka",

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T1 - Construction of trans-2,6-Disubstituted Piperidine Skeleton and Its Application to the Total Synthesis of (−)-Myrtine and trans-Piperidine-Type Poison-Frog Alkaloids

AU - Okada, Takuya

AU - Eguchi, Kenta

AU - Hasegawa, Fumiaki

AU - Ikhlaq, Mir Mohd

AU - Yoshikawa, Takahiro

AU - Toyooka, Naoki

PY - 2025/2/21

Y1 - 2025/2/21

N2 - We have succeeded in constructing a trans-2,6-disubstituted piperidine (trans-2,6-DP) skeleton by treatment of allylsilane derivative 2 with TMSOTf. Our designed trans-2,6-DP 1 has oxygen functional groups at the 2- and 6-positions and an exo-methylene moiety at the 4-position and is expected to be applied not only to the synthesis of various natural products but also as an excellent chiral building block with pseudo-symmetry. To demonstrate the versatility of 1, the total synthesis of (−)-myrtin and trans-piperidine-type poison-frog alkaloid 213A and 213B was accomplished.

AB - We have succeeded in constructing a trans-2,6-disubstituted piperidine (trans-2,6-DP) skeleton by treatment of allylsilane derivative 2 with TMSOTf. Our designed trans-2,6-DP 1 has oxygen functional groups at the 2- and 6-positions and an exo-methylene moiety at the 4-position and is expected to be applied not only to the synthesis of various natural products but also as an excellent chiral building block with pseudo-symmetry. To demonstrate the versatility of 1, the total synthesis of (−)-myrtin and trans-piperidine-type poison-frog alkaloid 213A and 213B was accomplished.

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DO - 10.1021/acs.joc.4c02976

M3 - 学術論文

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SN - 0022-3263

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ER -

Construction of trans-2,6-Disubstituted Piperidine Skeleton and Its Application to the Total Synthesis of (−)-Myrtine and trans-Piperidine-Type Poison-Frog Alkaloids

Abstract

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