| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5218948 | Tetrahedron | 2012 | 9 Pages |
Abstract
A flexible enantioselective approach to polyhydroxylated prolinol derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S,4R)-8, derived from d-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a-e and 9h-j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65-91%. These reductive hydroxyalkylations are highly diastereoselective in establishing the C-4 stereogenic center. By this way, the asymmetric syntheses of (â)-8a-epi-swainsonine (4) and (â)-8,8a-di-epi-swainsonine (5) have been achieved.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hong-Kui Zhang, Shou-Qiang Xu, Jia-Jia Zhuang, Jian-Liang Ye, Pei-Qiang Huang,