Total Synthesis of Hinckdentine A

Jiye Jeon; Sang Eun Lee; Cheol Hong Cheon

doi:10.1021/acs.orglett.1c00323

Total Synthesis of Hinckdentine A

Jiye Jeon, Sang Eun Lee, Cheol Hong Cheon

Department of Chemistry

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

17 Citations (Scopus)

Abstract

The total synthesis of (±)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A.

Original language	English
Pages (from-to)	2169-2173
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.1c00323
Publication status	Published - 2021 Mar 19

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Total Synthesis of Hinckdentine A",

abstract = "The total synthesis of (±)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A. ",

author = "Jiye Jeon and Lee, {Sang Eun} 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-2014-011165, Center for New Directions in Organic Synthesis). J.J. acknowledges financial support from the NRF-2018 Fostering Core Leaders of the Future Basic Science Program/Global Ph.D. Fellowship Program funded by the Korean Government. Publisher Copyright: {\textcopyright} ",

year = "2021",

month = mar,

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doi = "10.1021/acs.orglett.1c00323",

language = "English",

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journal = "Organic Letters",

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T1 - Total Synthesis of Hinckdentine A

AU - Jeon, Jiye

AU - Lee, Sang Eun

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-2014-011165, Center for New Directions in Organic Synthesis). J.J. acknowledges financial support from the NRF-2018 Fostering Core Leaders of the Future Basic Science Program/Global Ph.D. Fellowship Program funded by the Korean Government. Publisher Copyright: ©

PY - 2021/3/19

Y1 - 2021/3/19

N2 - The total synthesis of (±)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A.

AB - The total synthesis of (±)-hinckdentine A is described herein. A cyanide-catalyzed imino-Stetter reaction of the aldimine derived from ethyl 2-amino-3,5-dibromocinnamate and 5-bromo-2-nitrobenzaldehyde followed by oxidative rearrangement afforded a 2,2-disubstituted 3-indolinone derivative containing the carbon skeleton and all of the functional groups present in the natural product correctly positioned, including three bromine atoms. Subsequent D-ring formation and seven-membered C-ring construction completed the total synthesis of hinckdentine A.

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U2 - 10.1021/acs.orglett.1c00323

DO - 10.1021/acs.orglett.1c00323

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VL - 23

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JO - Organic Letters

JF - Organic Letters

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ER -

Total Synthesis of Hinckdentine A

Abstract

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