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Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids.

Abstract:

A range of enantiopure polyhydroxylated piperidines, including (2R,3S,4R)-dihydroxypipecolic acid, (-)-3-epi-fagomine, (2S,3S,4R)-dihydroxyhomopipecolic acid, (2S,3R,4R)-dihydroxyhomopipecolic acid, and two trihydroxy-substituted homopipecolic acids, have been prepared using diastereoselective olefinic oxidations of a range of enantiopure tetrahydropyridines as the key step. The requisite substrates were readily prepared from tert-butyl sorbate using our diastereoselective hydroamination or a...

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Publication status:
Published

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Publisher copy:
10.1021/jo501952t

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Publisher:
American Chemical Society
Journal:
Journal of organic chemistry More from this journal
Volume:
79
Issue:
22
Pages:
10932-10944
Publication date:
2014-11-01
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Pubs id:
pubs:488435
UUID:
uuid:f2385bdd-454f-4381-8ba8-0e22ad4ee155
Local pid:
pubs:488435
Source identifiers:
488435
Deposit date:
2014-12-20

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