Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Boronic Acid-Catalyzed Final-Stage Site-Selective Acylation for the Total Syntheses of O-3′-Acyl Bisabolol β-D-Fucopyranoside Natural Products and Their Analogues
Yuki NakamuraTakayuki OchiaiKazuishi MakinoNaoyuki Shimada
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2021 Volume 69 Issue 3 Pages 281-285

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Abstract

The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′-isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole-containing boronic acid catalysts as a key step. This synthetic method was also effective for the syntheses of unnatural analogues with modified acyl side chains or carbohydrate moiety.

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