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Diversity oriented concise asymmetric synthesis of azasugars: a facile access to l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Dec2015, Vol. 56 Issue 48, p6659-6663. 5p. - Publication Year :
- 2015
-
Abstract
- Diversity oriented concise asymmetric syntheses of l -2,3- trans -3,4- cis -dihydroxyproline and (3 S ,5 S )-3,4,5-trihydroxypiperidine have been developed from ( R )-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de . The (2 R ,3 R ,4 S )-2,3-dihydroxypentanoate derivative 15 was subsequently converted to natural pyrrolidine azasugar 1 and non-natural piperidine azasugar 4 under cascade reaction conditions in good yields. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 56
- Issue :
- 48
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 110701540
- Full Text :
- https://doi.org/10.1016/j.tetlet.2015.10.013