对映选择性全合成天然环烯醚萜。
Enantioselective total synthesis of a natural iridoid.
机构信息
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
出版信息
Org Lett. 2011 Jul 1;13(13):3344-7. doi: 10.1021/ol201089f. Epub 2011 May 27.
PMID:21619009
Abstract
The first total synthesis of 6-hydroxy-7-(hydroxymethyl)-4-methylenehexahydrocyclopenta[c]pyran-1(3H)-one has been accomplished. A key feature of the synthesis includes facile construction of the bicyclic lactone intermediate via intramolecular Pd(0)-catalyzed allylic alkylation and the efficient transformation of this intermediate into the iridoid skeleton employing silicon tethered radical cyclization.
摘要
6-羟基-7-(羟甲基)-4-亚甲基六氢环戊并[c]吡喃-1(3H)-酮的首次全合成已经完成。该合成的一个关键特点是通过分子内 Pd(0)催化的烯丙基烷基化反应轻松构建双环内酯中间体，并利用硅基自由基环化反应有效地将该中间体转化为环烯醚萜骨架。
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