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Synthesis 2019; 51(19): 3747-3757
DOI: 10.1055/s-0039-1690000
paper
© Georg Thieme Verlag Stuttgart · New York

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

Anton S. Makarov
a   Perm State University, Bukireva st. 15, 614990 Perm, Russian Federation   Email: mu@psu.ru
,
Anna E. Kekhvaeva
a   Perm State University, Bukireva st. 15, 614990 Perm, Russian Federation   Email: mu@psu.ru
,
Petrakis N. Chalikidi
b   K. L. Khetagurov North Ossetian State University, Vatutina st. 46, 362025 Vladikavkaz, Russian Federation
,
Vladimir T. Abaev
b   K. L. Khetagurov North Ossetian State University, Vatutina st. 46, 362025 Vladikavkaz, Russian Federation
,
Igor V. Trushkov
c   Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela st. 1, 117997 Moscow, Russian Federation
d   N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation
,
Maxim G. Uchuskin  ∗
a   Perm State University, Bukireva st. 15, 614990 Perm, Russian Federation   Email: mu@psu.ru
› Author AffiliationsThis work was supported by the Russian Science Foundation (Grant No. 17-73-10349).
Further Information

Publication History

Received: 17 April 2019

Accepted after revision: 13 June 2019

Publication Date:
03 July 2019 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690000.
  • Supporting Information
 

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