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Multicomponent Synthesis of 6H-Dibenzo[b,d]pyran-6-ones and a Total Synthesis of Cannabinol
Organic Letters ( IF 4.9 ) Pub Date : 2011-12-15 00:00:00 , DOI: 10.1021/ol2030636
Penchal Reddy Nandaluru 1 , Graham J. Bodwell 1
Affiliation  

A multicomponent domino reaction that affords 6H-dibenzo[b,d]pyran-6-ones is reported. The overall transformation consists of six reactions: Knoevenagel condensation, transesterification, enamine formation, an inverse electron demand Diels–Alder (IEDDA) reaction, 1,2-elimination, and transfer hydrogenation. Both the diene and dienophile for the key inverse electron demand Diels–Alder (IEDDA) step are generated in situ by secondary amine-mediated processes. In most cases, the yields (10–79%) are considerably better than those obtained using a stepwise process. This methodology is employed in a concise total synthesis of cannabinol.

中文翻译:

6 H-二苯并[ b,d ]吡喃-6-酮的多组分合成及大麻酚​​的总合成

报道了提供6 H-二苯并[ b,d ]吡喃-6-酮的多组分多米诺反应。整个转化过程包括六个反应:诺文奇缩合,酯交换反应,烯胺形成,电子反需求Diels-Alder(IEDDA)反应,1,2-消除反应和转移加氢反应。关键的逆电子需求Diels–Alder(IEDDA)步骤中的二烯和亲二烯体都是通过仲胺介导的过程原位生成的。在大多数情况下,产率(10-79%)要比逐步法获得的要好得多。该方法用于大麻酚的简明全合成。
更新日期:2011-12-15
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