| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1388855 | Carbohydrate Research | 2009 | 4 Pages |
Abstract
A seven-step total synthesis of Hagen’s gland lactones 1 and 2 starting from 1,2-O-isopropylidene-α-d-xylofuranose 3 is reported. The success of this short and practical synthesis depends on the use of two key reactions: a stereoselective nucleophilic substitution at the anomeric position of 5 and 6, which allowed the construction of the γ-lactone ring, and an alkyl substitution reaction on tosylated compound 4, which permitted the carbon chain elongation of the tetrahydrofuran ring appendage at C-6.
Graphical abstractA short and practical synthesis of Hagen’s gland lactones is reported.Figure optionsDownload full-size imageDownload as PowerPoint slide
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Evelyn Paz-Morales, Ruth Melendres, Fernando Sartillo-Piscil,