Total Synthesis and Revision of Stereochemistry of a Natural Benzo[g]isochromene Stereodiad Isolated from Rubia philippinensis,Organic Letters

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Total Synthesis and Revision of Stereochemistry of a Natural Benzo[g]isochromene Stereodiad Isolated from Rubia philippinensis
Organic Letters ( IF 4.9 ) Pub Date : 2024-03-21 , DOI: 10.1021/acs.orglett.4c00553
Rahul Choudhury _{1,

2} , Satya Ravi Teja Miriyala _{2,

3} , K R Resmi ₄ , Balasubramanian Sridhar _{2,

4} , S R Krishna Murthy Kasa ₅ , D Srinivasa Reddy _{2,

3}

Affiliation

This study presents a total synthesis and revision of the stereochemical configuration of the conformationally flexible natural product benzo[g]isochromene stereodiad alongside its diastereomeric counterparts. The highlights of the synthesis are the TiCl₄-mediated diastereoselective aldol reaction, Pd-catalyzed lactonization, and Schmidt glycosidation. Our efforts using total synthesis disclosed herein proved that a previously assigned structure required revision.

中文翻译：

菲律宾茜草中天然苯并[g]异色烯立体二甲体的全合成和立体化学修正

这项研究提出了构象灵活的天然产物苯并[ g ]异色烯立体二元及其非对映异构体的立体化学构型的全合成和修订。合成的亮点是TiCl ₄介导的非对映选择性羟醛反应、Pd催化的内酯化和Schmidt糖苷化。我们使用本文公开的全合成的努力证明了先前分配的结构需要修改。

更新日期：2024-03-21

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