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- Title
Diastereoselective Overman Rearrangement of an L-Ascorbic-Acid-Derived Allylic Alcohol: Application in the Synthesis of (+)-1,2-Di- epi-swainsonine and a Tetrahydroxypyrrolizidine.
- Authors
Rajasekaran, Parasuraman; Ansari, Alafia A.; Vankar, Yashwant D.
- Abstract
Differently substituted ascorbic-acid-derived allylic alcohols were used to study the Overman rearrangement under thermal and palladium-catalysed conditions. It was found that protection of the δ alcohol substituent as a a tert-butyldimethylsilyl ether followed by Overman rearrangement using PdCl2(MeCN)2 and p-benzoquinone at room temperature gave the best yield of the rearranged product in a highly diastereoselective manner. This rearrangement has been applied in the synthesis of (+)-1,2-di- epi-swainsonine and a tetrahydroxypyrrolizidine.
- Subjects
PALLADIUM; SWAINSONINE; GLYCOSIDASE inhibitors; INDOLE alkaloids; VITAMIN C
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 13, p2902
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500129