Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile
Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile
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DOI：
10.1021/jo800467e
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发表时间：
2008-06-20
影响因子：
3.6
通讯作者：
Opatz, Till
中科院分区：
文献类型：
--
作者：
Liermann, Johannes C.;Opatz, Till
1，2，3，4-四氢异喹啉-1-腈可作为一锅法合成5，6-二氢吡咯并[2，1a]异喹啉和1-苄基-3，4-二氢异喹啉的起始原料。后者化合物在短的反应序列中转化为片螺素G三甲基醚和片螺素U。该方法允许引入酸敏感性保护基团用于酚羟基官能团，所述酚羟基官能团将在经典的Bischler-Napieralski反应的苛刻条件下裂解。
1,2,3,4-Tetrahydroisoquinoline-1-carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.