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Hydroboration of C-arylglucals. Synthesis of the β-C-arylglucoside nucleus of chaetiacandin

✍ Scribed by Richard W. Friesen; Anand K. Daljeet

Book ID
104228300
Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
280 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

The hydroborations of the C-arylglucals 3a-c obtained from palladium catalyzed coupling reactions, provide the corresponding p-C-arylglucosides. Depending upon the conditions chosen for the oxidative workup, either the alcohols 5a-c or the products resulting from silyl migration (4a-c) are readily obtained. The palladium catalyzed coupling-hydroboration sequence has been applied to the synthesis of the p-C-arylglucoside nucleus of chaetiacandin, an anti-yeast antibiotic of the papulacaudin family.

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