PALLADIUM(II)-ASSISTED DIFUNCTIONALIZATION OF MONOOLEFINS - TOTAL SYNTHESIS OF (+)-NEGAMYCIN AND (-)-5-EPI-NEGAMYCIN

被引：42

作者：

MASTERS, JJ ^{[1
]}

HEGEDUS, LS ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 17期

关键词：

D O I：

10.1021/jo00069a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Negamycin and (-)-5-epi-negamycin were synthesized by a process involving the palladium-(II)-assisted alkylation of an optically active ene carbamate followed by carbonylative coupling to a trialkylvinyltin. The synthesis of (+)-negamycin was completed in 15 steps with an overall yield of 13%. The synthesis of (-)-5-epi-negamycin was completed in 12 steps with an overall yield of 20%. In preparing these compounds, a highly diastereoselective reduction of an unsaturated ketone and an efficient intramolecular Mitsunobu reaction were also carried out.

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页码：4547 / 4554

页数：8

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