A Meisenheimer rearrangement approach to bridgehead hydroxylated tropane alkaloid derivatives

被引:28
作者
Bremner, JB [1 ]
Smith, RJ [1 ]
Tarrant, GJ [1 ]
机构
[1] PHYTEX AUSTRALIA PTY LTD,SYDNEY,NSW,AUSTRALIA
关键词
D O I
10.1016/0040-4039(95)02082-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermolysis of 3-t-butyldimethylsiloxy-8-methyl-8-azabicyclo[3.2.1]oct-6-ene N-oxide (11) and (12) in butyronitrile gave 3-t-butyldimethylsiloxy-9-methyl-8-oxa-9-azabicyclo[3.2.2]non-6-ene (13) which upon reductive N-O ring cleavage, hydrogenation, oxidation and deprotection yielded the 3-hydroxy analogue 8-methyl-8-azabicyclo[3.2.1]octane-1,3-diol (6a reversible arrow 6b) of the tropane alkaloid physoperavine.
引用
收藏
页码:97 / 100
页数:4
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