HYDROXY-DIRECTED KETONE REDUCTION - APPLICATION TO THE SYNTHESIS OF (+)-8,8A-DIEPICASTANOSPERMINE

被引:16
作者
THOMPSON, SHJ
SUBRAMANIAN, RS
ROBERTS, JK
HADLEY, MS
GALLAGHER, T
机构
[1] UNIV BRISTOL,SCH CHEM,BRISTOL BS8 1TS,AVON,ENGLAND
[2] SMITHKLINE BEECHAM PHARMACEUT,HARLOW CM19 5AD,ESSEX,ENGLAND
关键词
D O I
10.1039/c39940000933
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reduction of heterocyclic-derived aldol adducts 2 and 3 using NaBH(OAc)(3) is stereoselective and proceeds via a hydroxy-directed mechanism to give 6 and 7, respectively, thereby complementing the stereoselectivity available with NaBH4; a synthesis of (+)-8,8a-diepicastanospermine 11 from diol 6 is described.
引用
收藏
页码:933 / 934
页数:2
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