ENANTIOSELECTIVE TOTAL SYNTHESIS OF A NATURAL NORSESQUITERPENE OF THE CALAMENENE GROUP BY A SILANE-TERMINATED INTRAMOLECULAR HECK REACTION

被引：0
|
作者：
TIETZE, LF
RASCHKE, T
机构：
来源：
SYNLETT | 1995年 / 06期
关键词：
HECK REACTION; ENANTIOSELECTIVE; NORSESQUITERPENES; ALLYLSILANES; TETRALINES; HYDROXYLATION;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of the natural norsesquiterpene 7-desmethyl-2-methoxycalamenene 1 by an enantioselective silane-terminated Heck reaction is described. The substrate 2 used for the Heck reaction was synthesized in 7 steps from 3-(3-methoxyphenyl) propanol in 41 % yield. Heck reaction of 2 with Pd-2(dba)(3) . CHCl3, (R)-BINAP and Ag3PO4 gives 8 in 91 % yield with 92 % ee, which after hydroxylation, transformation in the p-toluenesulfonate and methylation with Me(2)CuLi gave 1 in 36 % yield.
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页码：597 / 598
页数：2
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