The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone
The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone
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DOI：
10.1021/ja061853f
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发表时间：
2006-06-21
影响因子：
15
通讯作者：
Stoltz, Brian M.
中科院分区：
文献类型：
--
作者：
McFadden, Ryan M.;Stoltz, Brian M.
本文报道了首次对映体选择性全合成(+)-二色酮，确认了天然产物的绝对构型。这条无保护基团的路线首次在天然产物全合成的背景下应用了我们的对映体选择性Tsuji烯丙基化。此外，这种从商业材料中制备该分子的11步步骤具有新颖的熊田芳构化策略和将苯酚转化为羟基对苯二酚的快速序列。
Herein we report the first enantioselective total synthesis of (+)-dichroanone, confirming the absolute configuration of the natural product. This protecting group-free route features the first application of our enantioselective Tsuji allylation in the context of a natural product total synthesis. Additionally, this 11-step preparation of the molecule from commercial material features a novel Kumada-aromatization strategy and a rapid sequence for the conversion of a phenol to a hydroxy-p-benzoquinone.