Synthesis of (2S,4S,5S)-5-hydroxy-4-methylpipecolic acid via amide methylenation of 5-hydroxy-4-methyl-2-piperidinone with dimethyltitanocene

被引：15

作者：

Herdeis, C

Heller, E

机构：

[1] Inst. Fur Pharm./Lebensmittelchemie, Universität Würzburg, D-97074 Würzburg, Am Hubland

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(97)00091-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(4S,5S)-5-hydroxy-4-methylpiperidine-2-one 4, readily available from S-glutamic acid, serves as a starting material for the synthesis of (2S,4S,SS)-5-hydroxy-4-methylpipecolic acid 12. The key step of this reaction sequence is the chemoselective methylenation of the amide carbonyl group of 6 with dimethyltitanocene to the exocyclic enecarbamate 7. Hydroboration/oxidation of the double bond resulted in the formation of all-cis alcohol 8 which was transformed via aldehyde to 12. (C) 1997 Elsevier Science Ltd.

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页码：1115 / 1121

页数：7

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