A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans

Anton S. Makarov; Anna E. Kekhvaeva; Petrakis N. Chalikidi; Vladimir T. Abaev; Igor V. Trushkov; Maxim G. Uchuskin

doi:10.1055/s-0039-1690000

Synthesis, Table of Contents

Synthesis 2019; 51(19): 3747-3757
DOI: 10.1055/s-0039-1690000

paper

A Simple Synthesis of Densely Substituted Benzofurans by Domino Reaction of 2-Hydroxybenzyl Alcohols with 2-Substituted Furans

Anton S. Makarov

^aPerm State University, Bukireva st. 15, 614990 Perm, Russian Federation Email: mu@psu.ru

,

Anna E. Kekhvaeva

^aPerm State University, Bukireva st. 15, 614990 Perm, Russian Federation Email: mu@psu.ru

,

Petrakis N. Chalikidi

^bK. L. Khetagurov North Ossetian State University, Vatutina st. 46, 362025 Vladikavkaz, Russian Federation

,

Vladimir T. Abaev

^bK. L. Khetagurov North Ossetian State University, Vatutina st. 46, 362025 Vladikavkaz, Russian Federation

,

Igor V. Trushkov

^cDmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela st. 1, 117997 Moscow, Russian Federation

^dN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation

,

Maxim G. Uchuskin ∗

^aPerm State University, Bukireva st. 15, 614990 Perm, Russian Federation Email: mu@psu.ru

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Abstract

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Abstract

The Brönsted acid-catalyzed cascade synthesis of densely substituted benzofurans from easily available salicyl alcohols and biomass-derived furans has been developed. The disclosed sequence includes the intermediate formation of 2-(2-hydroxybenzyl)furans that quickly rearrange into functionalized benzofurans. The established protocol was applied for the total synthesis of sugikurojinol B.

Key words

furan - benzofuran - rearrangement - sugikurojinol B

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References

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