Total synthesis of (+)-okaramine J featuring an exceptionally facile N-reverse-prenyl to C-prenyl Aza-Claisen rearrangement

被引:59
作者
Roe, JM
Webster, RAB
Ganesan, A [1 ]
机构
[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
[2] Pfizer Global Res & Dev, Vet Med, Sandwich CT13 9NJ, Kent, England
关键词
D O I
10.1021/ol034822n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Graphics The convergent total synthesis of (+)-okaramine J was achieved in a longest linear sequence of 12 steps from L-tryptophan tert-butyl ester. A key reaction was the acid-catalyzed room-temperature aza-Claisen rearrangement of a N-reverse-prenylated hexahydro[2,3-b]pyrroloindole to a C-prenylated derivative.
引用
收藏
页码:2825 / 2827
页数:3
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