An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin
An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin
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DOI：
10.1021/ol062067i
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发表时间：
2006-12-07
期刊：
影响因子：
5.2
通讯作者：
Danishefsky, Samuel J.
中科院分区：
文献类型：
--
作者：
Cook, Silas P.;Danishefsky, Samuel J.
高价碘介导的氧化脱芳构化/Diels-Alder级联的背景下，天然产物11-O-脱苯甲酰tashironin进行了检查。有趣的是，Diels-Alder反应的区域选择性可以通过改变亲二烯体来完全改变。在氧化脱芳构化过程中烯丙醇的捕获产生五元缩醛，而丙二烯醇的捕获产生六元缩醛。
The hypervalent iodine-mediated oxidative dearomatization/Diels-Alder cascade was examined in the context of the natural product 11-O-debenzoyltashironin. Interestingly, the regioselectivity of the Diels-Alder reaction can be completely switched by changing the dienophile. Trapping of allyl alcohols during the oxidative dearomatization gives rise to the five-membered acetal, while trapping of allenyl alcohols results in the six-membered acetal.