De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A

Chenlong Zhu; Juntian Zhang; Thomas R. Hoye

doi:10.1021/acs.orglett.1c02752

De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A

Chenlong Zhu, Juntian Zhang, Thomas R. Hoye

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

9 Scopus citations

Abstract

Here we describe the use of the hexadehydro-Diels-Alder (HDDA) reaction for the de novo construction of the isoindolinone scaffold and its application to the synthesis of the title natural products. The key isoindolinone-forming HDDA reaction involved an unprecedented substrate motif in which an amide carbonyl group was conjugated to the 4π1,3-diyne component. In addition, a dimethylsilyl (-SiMe2H) substituent was exploited to trigger a Fleming-Tamao-Kumada oxidation for the installation of an essential phenolic hydroxyl group.

Original language	English (US)
Pages (from-to)	7550-7554
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.1c02752
State	Published - Oct 1 2021

Bibliographical note

Funding Information:
This research was supported by a grant from the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097). Some of the NMR spectra were obtained with an instrument funded in part by the NIH Shared Instrumentation Grant program (S10OD011952). Mass spectra were obtained in the Analytical Biochemistry Shared Resource laboratory in the Masonic Cancer Center at the University of Minnesota; that instrumentation was partially funded by a Cancer Center Support Grant (CA-77598). Computational studies were made possible with resources provided by the University of Minnesota Supercomputing Institute (MSI).

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© 2021 American Chemical Society.

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title = "De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A",

abstract = "Here we describe the use of the hexadehydro-Diels-Alder (HDDA) reaction for the de novo construction of the isoindolinone scaffold and its application to the synthesis of the title natural products. The key isoindolinone-forming HDDA reaction involved an unprecedented substrate motif in which an amide carbonyl group was conjugated to the 4π1,3-diyne component. In addition, a dimethylsilyl (-SiMe2H) substituent was exploited to trigger a Fleming-Tamao-Kumada oxidation for the installation of an essential phenolic hydroxyl group.",

author = "Chenlong Zhu and Juntian Zhang and Hoye, {Thomas R.}",

note = "Funding Information: This research was supported by a grant from the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097). Some of the NMR spectra were obtained with an instrument funded in part by the NIH Shared Instrumentation Grant program (S10OD011952). Mass spectra were obtained in the Analytical Biochemistry Shared Resource laboratory in the Masonic Cancer Center at the University of Minnesota; that instrumentation was partially funded by a Cancer Center Support Grant (CA-77598). Computational studies were made possible with resources provided by the University of Minnesota Supercomputing Institute (MSI). Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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AU - Zhu, Chenlong

AU - Zhang, Juntian

AU - Hoye, Thomas R.

N1 - Funding Information: This research was supported by a grant from the National Institutes of General Medical Sciences of the U.S. Department of Health and Human Services (R35 GM127097). Some of the NMR spectra were obtained with an instrument funded in part by the NIH Shared Instrumentation Grant program (S10OD011952). Mass spectra were obtained in the Analytical Biochemistry Shared Resource laboratory in the Masonic Cancer Center at the University of Minnesota; that instrumentation was partially funded by a Cancer Center Support Grant (CA-77598). Computational studies were made possible with resources provided by the University of Minnesota Supercomputing Institute (MSI). Publisher Copyright: © 2021 American Chemical Society.

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Y1 - 2021/10/1

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AB - Here we describe the use of the hexadehydro-Diels-Alder (HDDA) reaction for the de novo construction of the isoindolinone scaffold and its application to the synthesis of the title natural products. The key isoindolinone-forming HDDA reaction involved an unprecedented substrate motif in which an amide carbonyl group was conjugated to the 4π1,3-diyne component. In addition, a dimethylsilyl (-SiMe2H) substituent was exploited to trigger a Fleming-Tamao-Kumada oxidation for the installation of an essential phenolic hydroxyl group.

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De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A

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