TOTAL ASYMMETRIC SYNTHESES OF (+)-BLASTMYCINONE AND RELATED GAMMA-LACTONES

被引:50
作者
NISHIDE, K [1 ]
ARAMATA, A [1 ]
KAMANAKA, T [1 ]
INOUE, T [1 ]
NODE, M [1 ]
机构
[1] KYOTO PHARMACEUT UNIV,KYOTO 607,JAPAN
关键词
D O I
10.1016/S0040-4020(01)85556-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The freeze of the conformer was realized by the introduction of an alkyl substituent at alpha-position of tetronic acid using a readily available none C-2 chiral auxiliary (SMP or RMP), and conducted the desired asymmetric gamma-methylation. Its application to expeditious total syntheses of (+)-blastmycinone (I) and (-)-3-epi-blastmycinone (2), and to the first total synthesis of (+)-(3R,4R,5R)-4-acetoxy-5-methyl-3-tetradecyltetrahydro-2(5H)-furanone (3) was described.
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收藏
页码:8337 / 8346
页数:10
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