SYNTHESIS OF THE SECURINEGA ALKALOIDS (+/-)-NORSECURININE AND (+/-)-NIRURINE FROM 3-HYDROXYPYRIDINE

被引：36
|
作者：
MAGNUS, P [1 ]
RODRIGUEZLOPEZ, J [1 ]
MULHOLLAND, K [1 ]
MATTHEWS, I [1 ]
机构：
[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405
来源：
TETRAHEDRON | 1993年 / 49卷 / 36期
关键词：
D O I：
10.1016/S0040-4020(01)88027-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of the dihydropyridine 5 with fluoride anion resulted in in situ formation of the allenyldiene 4 which cyclized to the azabicyclo[2.2.2]octene 9. Subsequent elaboration to the alcohol 24 and rearrangement gave norsecurinine 2. The intermediate diol 16 was converted into prenirurine 34 which upon conversion into an N-oxide rapidly rearranged to give traces of nirurine 1 and norphyllanthine 38.
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收藏
页码：8059 / 8072
页数：14
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