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Concise Total Synthesis of (+)-Atlanticone C
Synlett ( IF 1.7 ) Pub Date : 2020-07-31 , DOI: 10.1055/s-0040-1707215
Thorsten Bach 1 , Johanna Proessdorf , Andreas Zech , Christian Jandl
Affiliation  

The first enantioselective total synthesis of (+)-atlanticone C is described. The complex tricyclic protoilludane core was rapidly assembled by a photochemical reaction cascade starting from an easily accessible indanone precursor (3 steps). Optimization of an enantioselective Corey–Bakshi–Shibata reduction permitted a catalytic chiral reso­lution of the racemic photoproduct (45% over two steps; up to 98% ee). The enantiomerically enriched photoproduct was efficiently transformed into the (+)-enantiomer of atlanticone C (10 steps; 18% yield), and the absolute configuration of naturally occurring (–)-atlanticone C was thereby determined.

中文翻译:

(+)-Atlanticone C的简明全合成

描述了 (+)-atlanticone C 的第一个对映选择性全合成。通过从易于获得的茚满酮前体(3 个步骤)开始的光化学反应级联快速组装复杂的三环原伊鲁丹核心。对映选择性 Corey-Bakshi-Shibata 还原的优化允许外消旋光产物的催化手性拆分(两步 45%;高达 98% ee)。富含对映异构体的光产物被有效地转化为大西洋酮 C 的 (+)-对映异构体(10 步;18% 的产率),从而确定了天然存在的 (-)-大西洋酮 C 的绝对构型。
更新日期:2020-07-31
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