Elucidation of the acid reactivity of polyhedral orthoformates for the synthesis of carbasugar derivatives
Open Access
- 16 June 2025
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in RSC Advances
- Vol. 15 (26) , 20734-20744
Abstract
Carbasugar-containing natural products such as uvaridacol L have a variety of bioactivities, motivating chemists to develop methods for their synthesis. The conversion of myo-inositol is one of the most efficient methods for the synthesis of carbasugars. However, selective conversion of myo-inositol derivatives remains to be explored. In our synthesis of uvaridacol L derivatives, we found that the methoxy olefin derivatives of orthoester-protected myo-inositols, the key synthetic intermediates of our study, exhibit differing reaction selectivities depending on their geometric isomerism and substituents. Here we present new insights that contribute to the synthesis of carbasugar-type derivatives by elucidating the mechanism of the selectivity using density functional theory (DFT) calculations.Keywords
Funding Information
- Japan Society for the Promotion of Science (19K07035, 22K06570)
- Shiono Wellness Foundation (R4-4)
- Vehicle Racing Commemorative Foundation (6110, 6231, 6297)
- Pharmaceutical Society of Japan
- Suntory Foundation for Life Sciences
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