Symmetry-based approach to oligostilbenoids

Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

Youngeun Jung, Dileep Kumar Singh, Ikyon Kim

Research output: Contribution to journalArticle

5 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 languageEnglish
Pages (from-to)2689-2693
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume12
DOIs
Publication statusPublished - 2016 Dec 12

Fingerprint

Alkynes
Cyclization
Biological Products
Aldehydes
Iodine
Esters
Alcohols
Molecules
diptoindonesin G
malibatol A
alkoxyl radical
benzofuran

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

@article{b8acac79c60443f2ae48cbb70ac393a1,
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",
year = "2016",
month = "12",
day = "12",
doi = "10.3762/bjoc.12.266",
language = "English",
volume = "12",
pages = "2689--2693",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

Symmetry-based approach to oligostilbenoids : Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G. / Jung, Youngeun; Singh, Dileep Kumar; Kim, Ikyon.

In: Beilstein Journal of Organic Chemistry, Vol. 12, 12.12.2016, p. 2689-2693.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Symmetry-based approach to oligostilbenoids

T2 - Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

AU - Jung, Youngeun

AU - Singh, Dileep Kumar

AU - Kim, Ikyon

PY - 2016/12/12

Y1 - 2016/12/12

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85008235622&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85008235622&partnerID=8YFLogxK

U2 - 10.3762/bjoc.12.266

DO - 10.3762/bjoc.12.266

M3 - Article

VL - 12

SP - 2689

EP - 2693

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -