Total Syntheses of rac- and (+)-Goniomitine

Eunjoon Park; Cheol Hong Cheon

doi:10.1002/adsc.201900801

Total Syntheses of rac- and (+)-Goniomitine

Eunjoon Park, Cheol Hong Cheon

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

13 Citations (Scopus)

Abstract

Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac- or (S)-indole-3-acetate carrying an α-vinyl-δ-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations. (Figure presented.).

Original language	English
Pages (from-to)	4888-4892
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	361
Issue number	21
DOIs	https://doi.org/10.1002/adsc.201900801
Publication status	Published - 2019 Nov 5

Bibliographical note

Funding Information:
This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF‐2018R1D1 A1 A02086110 and NRF‐2014‐011165, Center for New Directions in Organic Synthesis).

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Asymmetric synthesis
Biomimetic total synthesis
Cyanide
Imino-Stetter reaction
goniomitine

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201900801

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title = "Total Syntheses of rac- and (+)-Goniomitine",

abstract = "Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac- or (S)-indole-3-acetate carrying an α-vinyl-δ-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations. (Figure presented.).",

keywords = "Asymmetric synthesis, Biomimetic total synthesis, Cyanide, Imino-Stetter reaction, goniomitine",

author = "Eunjoon Park and Cheon, {Cheol Hong}",

note = "Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF‐2018R1D1 A1 A02086110 and NRF‐2014‐011165, Center for New Directions in Organic Synthesis). Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/adsc.201900801",

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T1 - Total Syntheses of rac- and (+)-Goniomitine

AU - Park, Eunjoon

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF‐2018R1D1 A1 A02086110 and NRF‐2014‐011165, Center for New Directions in Organic Synthesis). Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/11/5

Y1 - 2019/11/5

N2 - Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac- or (S)-indole-3-acetate carrying an α-vinyl-δ-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations. (Figure presented.).

AB - Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position, provided rac- or (S)-indole-3-acetate carrying an α-vinyl-δ-valerolactam scaffold at the 2-position, respectively. Subsequent saturation of the vinyl group, followed by treatment with DIBAL-H, afforded N-benzyl protected goniomitine. Final debenzylation provided the desired natural product after only three column separations. (Figure presented.).

KW - Asymmetric synthesis

KW - Biomimetic total synthesis

KW - Cyanide

KW - Imino-Stetter reaction

KW - goniomitine

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DO - 10.1002/adsc.201900801

M3 - Article

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SN - 1615-4150

VL - 361

SP - 4888

EP - 4892

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 21

ER -

Total Syntheses of rac- and (+)-Goniomitine

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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