Asymmetric Syntheses of (鈭?-3-epi-Fagomine, (2R,3S,4R)-Dihydroxypipecolic Acid, and Several Polyhydroxylated Homopipecolic Acids
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- 作者：Krist铆na Csatayov谩 ; Stephen G. Davies ; Ai M. Fletcher ; J. Gair Ford ; David J. Klauber ; Paul M. Roberts ; James E. Thomson
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：November 21, 2014
- 年：2014
- 卷：79
- 期：22
- 页码：10932-10944
- 全文大小：668K
- ISSN：1520-6904
文摘
A range of enantiopure polyhydroxylated piperidines, including (2R,3S,4R)-dihydroxypipecolic acid, (鈭?-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 aminohydroxylation protocols followed by ring-closing metathesis. After diastereoselective olefinic oxidation of the resultant enantiopure tetrahydropyridines and deprotection, enantiopure polyhydroxylated piperidines were isolated as single diastereoisomers (>99:1 dr) in good overall yield.