Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

Youngeun Jung; Dileep Kumar Singh; Ikyon Kim

doi:10.3762/bjoc.12.266

Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

Youngeun Jung, Dileep Kumar Singh, Ikyon Kim

Department of Pharmacy

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

11 Citations (Scopus)

Abstract

The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.

Original language	English
Pages (from-to)	2689-2693
Number of pages	5
Journal	Beilstein Journal of Organic Chemistry
Volume	12
DOIs	https://doi.org/10.3762/bjoc.12.266
Publication status	Published - 2016 Dec 12

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2014R1A2A1A11050491). This work was also supported in part by the Yonsei Research Fund of 2015 (project no.: 2015-12-0215).

Publisher Copyright:
© 2016 Jung et al.; licensee Beilstein-Institut.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.3762/bjoc.12.266

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title = "Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G",

abstract = "The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.",

author = "Youngeun Jung and Singh, {Dileep Kumar} and Ikyon Kim",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2014R1A2A1A11050491). This work was also supported in part by the Yonsei Research Fund of 2015 (project no.: 2015-12-0215). Publisher Copyright: {\textcopyright} 2016 Jung et al.; licensee Beilstein-Institut.",

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AU - Kim, Ikyon

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Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

Abstract

Bibliographical note

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