4.7 Article

An Alternative Synthesis of 1,1′-Bis-valienamine from D-Glucose

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 10, Pages 3522-3525

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo100474p

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Funding

  1. Centre of Novel Functional Molecules, The Chinese University of Hong Kong

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An alternative synthesis of 1,1 '-bis-valienamine 5, which was demonstrated to be a potent trehalase inhibitor, has been achieved from D-glucose in 12 steps with 15% overall yield via enone 12 as the key intermediate, involving a direct aldol reaction of a glucose-derived diketone and a palladium-catalyzed allylic coupling reaction as the key steps.

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