Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core.,The Journal of Organic Chemistry

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Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-08-27 , DOI: 10.1021/acs.joc.9b01596
Kassrin Tangdenpaisal ₁ , Poramate Songthammawat ₂ , Kornkamon Akkarasereenon ₂ , Kanokpish Chuayboonsong ₂ , Somsak Ruchirawat _{1,

2,

3} , Poonsakdi Ploypradith _{1,

2,

3}

Affiliation

In four steps from the tricyclic core, palodesangren B trimethyl ether and palodesangren D dimethyl ether could be synthesized in 29 and 18% overall yields, respectively. A reaction sequence comprising the regioselective MgCl2-mediated Casnati-Skattebøl ortho-formylation of phenol, Wittig methylenation, acryloylation, and Ru(II)-catalyzed ring-closing metathesis (RCM) led to the formation of the final 2H-pyran-2-one ring of the desired tetracyclic core.

中文翻译：

通过四氢苯并[c]吡喃并色酮核的2H-吡喃-2-酮的后期形成，完全合成帕洛丹桑BB三甲基醚和D二甲基醚。

在三环核的四个步骤中，可以分别以29％和18％的总产率合成palodesangren B三甲基醚和palodesangren D二甲基醚。包含区域选择性MgCl2介导的Casnati-Skattebøl苯酚的甲酰化，Wittig甲基化，丙烯酰化和Ru（II）催化的闭环复分解（RCM）的反应序列导致最终2H-pyran-2-的形成所需四环核的一个环。

更新日期：2019-08-27

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