A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids

Eunjoon Park; Cheolwoo Bae; Cheon Gyu Cho; Cheol Hong Cheon

doi:10.1021/acs.joc.0c02936

A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids

Eunjoon Park, Cheolwoo Bae, Cheon Gyu Cho, Cheol Hong Cheon

Department of Chemistry

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

1 Citation (Scopus)

Abstract

Total syntheses of the antirhine alkaloids are described. The cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde provided a 2-pyridinyl substituted indole-3-acetate, which was further converted into the corresponding indoloquinolizidinium intermediate through C-ring formation. Subsequent trans-selective installation of the homoallylic alcohol side-chain at C-15 in the resulting indoloquinolizidinium allowed the total syntheses of antirhine and its known epimer.

Original language	English
Pages (from-to)	4497-4511
Number of pages	15
Journal	Journal of Organic Chemistry
Volume	86
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.0c02936
Publication status	Published - 2021 Mar 19

ASJC Scopus subject areas

Organic Chemistry

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title = "A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids",

abstract = "Total syntheses of the antirhine alkaloids are described. The cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde provided a 2-pyridinyl substituted indole-3-acetate, which was further converted into the corresponding indoloquinolizidinium intermediate through C-ring formation. Subsequent trans-selective installation of the homoallylic alcohol side-chain at C-15 in the resulting indoloquinolizidinium allowed the total syntheses of antirhine and its known epimer. ",

author = "Eunjoon Park and Cheolwoo Bae and Cho, {Cheon Gyu} 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-2018R1D1A1A02086110 and NRF-2014-011165, Center for New Directions in Organic Synthesis). Publisher Copyright: {\textcopyright} ",

year = "2021",

month = mar,

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doi = "10.1021/acs.joc.0c02936",

language = "English",

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T1 - A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids

AU - Park, Eunjoon

AU - Bae, Cheolwoo

AU - Cho, Cheon Gyu

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-2018R1D1A1A02086110 and NRF-2014-011165, Center for New Directions in Organic Synthesis). Publisher Copyright: ©

PY - 2021/3/19

Y1 - 2021/3/19

N2 - Total syntheses of the antirhine alkaloids are described. The cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde provided a 2-pyridinyl substituted indole-3-acetate, which was further converted into the corresponding indoloquinolizidinium intermediate through C-ring formation. Subsequent trans-selective installation of the homoallylic alcohol side-chain at C-15 in the resulting indoloquinolizidinium allowed the total syntheses of antirhine and its known epimer.

AB - Total syntheses of the antirhine alkaloids are described. The cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde provided a 2-pyridinyl substituted indole-3-acetate, which was further converted into the corresponding indoloquinolizidinium intermediate through C-ring formation. Subsequent trans-selective installation of the homoallylic alcohol side-chain at C-15 in the resulting indoloquinolizidinium allowed the total syntheses of antirhine and its known epimer.

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U2 - 10.1021/acs.joc.0c02936

DO - 10.1021/acs.joc.0c02936

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

A Stereodivergent Strategy for Total Syntheses of Antirhine Alkaloids

Abstract

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