General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers

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

doi:10.1021/acs.orglett.0c00544

General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers

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

^*Corresponding author for this work

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

14 Citations (Scopus)

Abstract

A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (±)-antirhine, (±)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.

Original language	English
Pages (from-to)	2354-2358
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.0c00544
Publication status	Published - 2020 Mar 20

Bibliographical note

Funding Information:
This work was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165 Center for New Directions in Organic Synthesis).

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00544

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title = "General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers",

abstract = "A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (±)-antirhine, (±)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.",

author = "Cheolwoo Bae and Eunjoon Park and Cho, \{Cheon Gyu\} and Cheon, \{Cheol Hong\}",

note = "Funding Information: This work was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165 Center for New Directions in Organic Synthesis). Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.orglett.0c00544",

language = "English",

volume = "22",

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journal = "Organic Letters",

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AU - Bae, Cheolwoo

AU - Park, Eunjoon

AU - Cho, Cheon Gyu

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165 Center for New Directions in Organic Synthesis). Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/3/20

Y1 - 2020/3/20

N2 - A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (±)-antirhine, (±)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.

AB - A general synthetic strategy for antirhine alkaloids was developed in this study. The cyanide-catalyzed imino-Stetter reaction of ethyl 2-aminocinnamate and 4-bromopyridine-2-carboxaldehyde afforded the corresponding indole-3-acetic acid derivative. Subsequent formation of the six-membered C ring followed by trans-selective installation of the two-carbon unit at C-15 provided rapid access to the key intermediate. Stereoselective installation of substituents at C-20 allowed the total syntheses of (±)-antirhine, (±)-18,19-dihydroantirhine, and their 20-epimers, all of the known natural products in the antirhine family.

UR - https://www.scopus.com/pages/publications/85081657861

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DO - 10.1021/acs.orglett.0c00544

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JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

General Strategy for the Synthesis of Antirhine Alkaloids: Divergent Total Syntheses of (±)-Antirhine, (±)-18,19-Dihydroantirhine, and Their 20-Epimers

Abstract

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ASJC Scopus subject areas

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