Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 41, Pages 11966-11970Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504729
Keywords
acylation; glycosides; natural products; organocatalysis; synthetic methods
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Funding
- MEXT
- Grants-in-Aid for Scientific Research [26460007, 26221301, 15K18827] Funding Source: KAKEN
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The first total syntheses of multifidosides A-C have been achieved. The synthetic strategy is characterized by catalytic site-selective acylation of unprotected glycoside precursors in the final stage of the synthesis. High functional-group tolerance of the site-selective acylation, promoted by an organocatalyst, enabled the conventionally difficult molecular transformation in a predictable and reliable manner. An advantage of this strategy is to avoid the risks of undesired side reactions during the removal of the protecting groups at the final stage of the total synthesis.
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