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作为Diels-Alder Dienes的比斯基等价物

Isuru Dissanayake¹, Jacob D Hart¹, Emma C Becroft¹

¹Department of Chemistry, The University of Adelaide, Adelaide, SA 5005, Australia.

Journal of the American Chemical Society

|July 21, 2020

概括

在迪尔斯-阿尔德反应中,2,5- ((丁二甲基西) furan 作为多功能二烯,提供了轻度和高效的替代型基和基的合成. 这种方法也产生了para-iminoquinones,并使天然产品的合成成为可能.

科学领域:

有机化学
合成化学
反应方法

背景情况:

2,5--丁甲基西) 被认为是有效的邻近比斯基等价物.
这些化合物是循环添加反应,特别是迪尔斯-阿尔德反应的有价值的二烯.

研究的目的:

探索2,5-丁二甲基西) 在迪尔斯-阿尔德反应中的功用.
开发高度替代的基和相关化合物的融合合成.
证明这些衍生物在天然产品合成中的应用.

主要方法:

使用2,5--丁甲基西) furan作为二烯的Diels-Alder循环添加反应.
使用olefinic和acetylenic二烯基,包括.
一个涉及迪尔斯-阿尔德循环加法,环开放和复合的单序列.

主要成果:

不受保护的,高度替代的基的融合和温和合成.
通过使用乙烯基二烯醇成功合成了para-benzoquinones.
确定2,5-bis ((tert-butyldimethylsilyloxy) pyrroles作为对胺基合成的二烯.
神经保护剂 (±) - 印多斯塔丁的格拉姆尺度合成.

结论:

2,5- ((比斯特-丁甲基西) 是迪尔斯-阿尔德反应的高效二烯,为有价值的衍生物提供了温和的途径.
开发的方法为包括自然产品在内的复杂结构提供了有效的访问.
这种方法扩大了有机合成中的二烯等效的范围.

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