Total Synthesis of (±)-Exotine B

Bichu Cheng; Giulio Volpin; Johannes Morstein; Dirk Trauner

doi:10.1021/acs.orglett.8b01817

Total Synthesis of (±)-Exotine B

Bichu Cheng, Giulio Volpin, Johannes Morstein, Dirk Trauner

Chemistry

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

Abstract

The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products gleinadiene and coumurrayin are also reported.

Original language	English (US)
Pages (from-to)	4358-4361
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.8b01817
State	Published - Jul 20 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b01817

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title = "Total Synthesis of (±)-Exotine B",

abstract = "The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products gleinadiene and coumurrayin are also reported.",

author = "Bichu Cheng and Giulio Volpin and Johannes Morstein and Dirk Trauner",

note = "Funding Information: We thank New York University for financial support and Dr. Chin Lin (NYU) for assistance with NMR spectrometry and mass spectrometry. NMR spectra were acquired using the TCI cryoprobe supported by The National Institutes of Health (OD016343). J.M. thanks the German Academic Scholarship Foundation for a PhD fellowship and New York University for a MacCracken PhD fellowship. Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b01817",

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T1 - Total Synthesis of (±)-Exotine B

AU - Cheng, Bichu

AU - Volpin, Giulio

AU - Morstein, Johannes

AU - Trauner, Dirk

N1 - Funding Information: We thank New York University for financial support and Dr. Chin Lin (NYU) for assistance with NMR spectrometry and mass spectrometry. NMR spectra were acquired using the TCI cryoprobe supported by The National Institutes of Health (OD016343). J.M. thanks the German Academic Scholarship Foundation for a PhD fellowship and New York University for a MacCracken PhD fellowship. Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2018/7/20

Y1 - 2018/7/20

N2 - The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products gleinadiene and coumurrayin are also reported.

AB - The heterodimeric indole/coumarin natural product exotine B was synthesized for the first time. The carbon skeleton of the natural product was formed rapidly by a palladium-catalyzed Suzuki cross-coupling reaction and a gallium-catalyzed three-component [4 + 3] cycloaddition reaction. An alternative biosynthesis of exotine B is proposed based on the total synthesis. Improved syntheses of coumarin natural products gleinadiene and coumurrayin are also reported.

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Total Synthesis of (±)-Exotine B

Abstract

ASJC Scopus subject areas

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