Enantioselective Total Synthesis of Secalonic Acid E
Enantioselective Total Synthesis of Secalonic Acid E
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DOI：
10.1002/chem.201503593
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发表时间：
2015-11-16
影响因子：
4.3
通讯作者：
Tietze, Lutz F.
中科院分区：
文献类型：
--
作者：
Ganapathy, Dhandapani;Reiner, Johannes R.;Tietze, Lutz F.
首次对映选择性合成了含有二聚体四羟基蒽酮骨架的secalonic酸，使用甲氧基酚化合物的Wacker型环化反应形成具有季碳立体异构中心的手性色满，其ee> 99%。进一步的步骤是Sharpless二羟基化和Dieckmann缩合，得到四羟基蒽酮。最后一步钯催化的Suzuki二聚反应导致2，2 '-联苯酚键合，以8%的总收率在18步中完成对映选择性全合成secalonic酸E。
The first enantioselective synthesis of a secalonic acid containing a dimeric tetrahydroxanthenone skeleton is described, using a Wacker-type cyclization of a methoxyphenolic compound to form a chiral chroman with a quaternary carbon stereogenic center with > 99% ee. Further steps are a Sharpless dihydroxylation and a Dieckmann condensation to give a tetrahydroxanthenone. A late-stage one-pot palladium-catalyzed Suzuki-dimerization reaction leads to the 2,2'-biphenol linkage to complete the enantioselective total synthesis of secalonic acid E in 18 steps with 8% overall yield.