Synthesis of the racemic tetracyclic core of CP-225,917: use of a strain-assisted Cope rearrangement

被引:16
作者
Clive, DLJ [1 ]
Ou, L [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
Cope rearrangement; strain; anhydride; furan; sodium chlorite; ruthenium dioxide; bridgehead olefin;
D O I
10.1016/S0040-4039(02)00741-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Norbornene was converted via diketone 23 into the strained lactone 27; this was rearranged thermally to lactone 28, from which point the complete oxygenated core of CP-225,917 is accessible by deprotection and oxidation steps, including a new method for converting a furan system into a hydroxy butenolide. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:4559 / 4563
页数:5
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