摘要
研究了Ｎ－甲基－３－羟基吡啶盐与丙烯腈的１，３－偶极环加成反应．由环合产物经过氢化，还原得包公藤甲素的中间体８－甲基－２β－羟基－８－氮二环［３．２．１］辛烷－６－ｅｘｏ－腈．本合成路线具有高立体选择性．
The reaction of N methyl 3 hydroxypyridinium iodide with acrylonitrile has been studied. Under various reaction conditions, none of the desired cycloaddition product was resulted. Instead, a Michael addition product was obtained. Alternatively, the 1,3 dipolar cycloaddition was achieved by the reaction of N methyl 3 oxopyridinium betaine with acrylonitrile in THF with a high regioselectivity and stereoselectivity. This paper reports the synthesis of an intermediate 8 methyl 2 β hydroxy 8 azabicyclo 3.2.1 octane 6 exo carbonitrile of 6 exo (acetyoxy) 8 azabicyclo 3.2.1 octan 2 exo ol. This synthetic route involves two high stereoselective steps.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
1998年第5期737-740,共4页
Chemical Journal of Chinese Universities
基金
国家自然科学基金
广东省自然科学基金
关键词
包公藤甲素
偶极环加成
合成
exo (Acetyoxy) 8 azabicyclo 3.2.1 octan 2 exo ol
1
3 Dipolar cycloaddition
Synthesis
8 Methyl 2 β hydroxy 8 azabicyclo 3.2.1 octane 6 exo carbonitrile
