| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1387697 | Carbohydrate Research | 2016 | 5 Pages |
Abstract
•Unexpected rearrangement of enofuranosides to cyclopentanones.•The rearrangement is conducted upon hydrogenolysis of the anomeric benzyl group.•High yield and stereoselectivity on certain arabinofuranoside substrates.
During our synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Shenyou Nie, Xiaoping Chen, Yuyong Ma, Wei Li, Biao Yu,