A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction

Eunjoon Park; Cheol Hong Cheon

doi:10.1039/c7ob02691a

A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction

Eunjoon Park, Cheol Hong Cheon

Department of Chemistry

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

14 Citations (Scopus)

Abstract

A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf₂O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

Original language	English
Pages (from-to)	10265-10275
Number of pages	11
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	48
DOIs	https://doi.org/10.1039/c7ob02691a
Publication status	Published - 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction",

abstract = "A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.",

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

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2015R1D1A1A01057200, NRF-2017M2A8A4018045, and NRF-20100020209). C.-H. C. thanks the financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis).",

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doi = "10.1039/c7ob02691a",

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publisher = "Royal Society of Chemistry",

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T2 - Via a cyanide-catalyzed imino-Stetter reaction

AU - Park, Eunjoon

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2015R1D1A1A01057200, NRF-2017M2A8A4018045, and NRF-20100020209). C.-H. C. thanks the financial support from an NRF grant funded by the Korean Government (NRF-2014-011165, Center for New Directions in Organic Synthesis).

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Y1 - 2017

N2 - A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

AB - A new strategy applicable to the synthesis of indoloquinolizine natural products has been developed. A cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines, derived from 2-aminocinnamic acid derivatives and 2-pyridinecarboxaldehydes, provided indole-3-acetic acid derivatives bearing a pyridyl ring at the 2-position. Reduction of the carboxylic acid moiety to an alcohol followed by activation of the resulting alcohol with Tf2O or TsCl generated indoloquinolizinium salts, which were utilized as precursors for indoloquinolizine natural products. The advantage of this protocol was successfully demonstrated in the total syntheses of arborescidine A and nauclefidine.

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JO - Organic and Biomolecular Chemistry

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ER -

A general strategy for the synthesis of indoloquinolizine alkaloids: Via a cyanide-catalyzed imino-Stetter reaction

Abstract

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