Total synthesis of himandravine

被引:31
作者
Chackalamannil, S
Davies, R
McPhail, AT
机构
[1] Schering Plough Corp, Res Inst, Kenilworth, NJ 07033 USA
[2] Duke Univ, PM Gross Chem Lab, Durham, NC 27708 USA
关键词
D O I
10.1021/ol010038w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The first total synthesis of (+)-himandravine (1) is described, starting from (2S,6S)-cis-2-formyl-6-methyl-N-Boc-piperidine (8) in 11 linear steps and 17% overall yield. The key step involves a highly diastereoselective intramolecular Diels-Alder reaction of the key intermediate 5 that contains the entire latent carbon framework and functional group substitution of himandravine.
引用
收藏
页码:1427 / 1429
页数:3
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