A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction
A concise and convergent route to 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine ring cores by diastereoselective aza-Diels-Alder reaction
复制标题
DOI：
10.1021/ol0260021
复制
发表时间：
2002-05-30
期刊：
影响因子：
5.2
通讯作者：
Valdés, C
中科院分区：
文献类型：
--
作者：
Barluenga, J;Mateos, C;Valdés, C
[图]描述了5,8-二取代吲哚吡啶和1,4-喹啉吡啶支架的快速合成。合成途径的关键步骤是2-氨基二烯与n -烯丙基或n -纯烯丙基醛二胺的aza- diols - alder反应和合环复合反应。双环生物碱类似物具有完全非对映选择性，并通过共同的途径得到。
[GRAPHICS]A short and convergent synthesis of 5,8-disubstituted indolizidine and 1,4-quinolizidine scaffolds is described. The key steps of the synthetic pathway are the aza-Diels-Alder reaction of a 2-aminodiene with an N-allyl or N-homoallylaldimine and a ring-closing metathesis. The bicyclic alkaloid analogues are obtained with total diastereoselectivity and through a common pathway.