Total synthesis of breviscapin B <i>via</i> intramolecular dehydrative etherification

The total synthesis of breviscapin B, a norlignan natural product having an unusual 2,2-diaryltetrahydrofuran skeleton, has been achieved <i>via</i> intramolecular dehydrative Williamson ether synthesis as a key step. The use of a combination of <i>p</i>-TsOH·H<sub>2</sub>O and polyfluorinated alcohol was found as an effective method for the synthesis of 2-aryl-substituted saturated oxygen heterocycles.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00350d
Citations
3
Primary Topic
Traditional and Medicinal Uses of Annonaceae
Type
article
Field-Weighted Citation Impact
3.34

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article

Total synthesis of breviscapin B via intramolecular dehydrative etherification

Masahiro Anada, Shunsuke Sueki, Kosho Makino, Chiharu Nogami
3 citations
Organic & Biomolecular Chemistry
Traditional and Medicinal Uses of Annonaceae
3.34
article

Total synthesis of breviscapin B via intramolecular dehydrative etherification

Masahiro Anada, Shunsuke Sueki, Kosho Makino, Chiharu Nogami
article en
3 citations

Abstract

The total synthesis of breviscapin B, a norlignan natural product having an unusual 2,2-diaryltetrahydrofuran skeleton, has been achieved <i>via</i> intramolecular dehydrative Williamson ether synthesis as a key step. The use of a combination of <i>p</i>-TsOH·H<sub>2</sub>O and polyfluorinated alcohol was found as an effective method for the synthesis of 2-aryl-substituted saturated oxygen heterocycles.

Organic & Biomolecular ChemistryVol. 23(21)
Musashino University (JP)
Musashino University, Japan Society for the Promotion of Science
Openalex Percentile: Top 9%
Traditional and Medicinal Uses of Annonaceae
3.34
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