Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

Se Hyun Kwon; Hong Ahn Seo; Cheol Hong Cheon

doi:10.1021/acs.orglett.6b02597

Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

Se Hyun Kwon, Hong Ahn Seo, Cheol Hong Cheon

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69 Citations (Scopus)

Abstract

The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).

Original language	English
Pages (from-to)	5280-5283
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.6b02597
Publication status	Published - 2016 Oct 21

Bibliographical note

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

Publisher Copyright:
© 2016 American Chemical Society.

Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization",

abstract = "The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).",

author = "Kwon, {Se Hyun} and Seo, {Hong Ahn} 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- 2015R1D1A1A01057200 and NRF-20100020209). C.-H.C. is also thankful for financial support from an NRF grant funded by the Korean Government (NRF-2014-011165; Center for New Directions in Organic Synthesis). Publisher Copyright: {\textcopyright} 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

year = "2016",

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doi = "10.1021/acs.orglett.6b02597",

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AU - Kwon, Se Hyun

AU - Seo, Hong Ahn

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- 2015R1D1A1A01057200 and NRF-20100020209). C.-H.C. is also thankful for financial support from an NRF grant funded by the Korean Government (NRF-2014-011165; Center for New Directions in Organic Synthesis). Publisher Copyright: © 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/10/21

Y1 - 2016/10/21

N2 - The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).

AB - The total synthesis of rutaecarpine (1) and luotonin A (2) is described through controlled cyclization of a common aldimine intermediate 5 derived from ethyl-2-aminocinnamate and quinazolinone-2-carbaldehyde. The cyanide-mediated imino-Stetter reaction of aldimine 5 provided the corresponding indole derivative 3, from which the total synthesis of rutaecarpine (1) was completed via the formation of a 6-membered C-ring. On the other hand, microwave-assisted thermal 6π-electrocyclization of the common intermediate 5, followed by the formation of a 5-membered C′-ring, allowed the completion of the total synthesis of luotonin A (2).

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Total Synthesis of Luotonin A and Rutaecarpine from an Aldimine via the Designed Cyclization

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