Total Synthesis of Salviachinensine A Using a Matteson Homologation Approach

被引：0

作者：

Kempf, Merlin ^{[1
]}

Andler, Oliver ^{[1
]}

Kazmaier, Uli ^{[1
]}

机构：

[1] Saarland Univ, Organ Chem, Campus C4-2, DE-66123 Saarbrucken, Germany

来源：

HELVETICA CHIMICA ACTA | 2023年 / 106卷 / 10期

关键词：

boron; boronic esters; Chinese medicine; Matteson homologation; natural products; Friedel-Crafts alkylation; CHLORO BORONIC ESTERS; CHIRAL DIRECTOR; ACID; ZINC;

D O I：

10.1002/hlca.202300136

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Salviachinensine A, a natural product obtained from the Chinese medicinal plant Salvia chinensis, was synthesized for the first time by employing Donald Matteson's boronic ester homologation. The use of (R,R)-dicyclohexylethane-1,2-diol (DICHED) enabled the generation of the required stereogenic centers in a highly stereoselective fashion. Salviachinensine A was formed in a one-pot protecting group cleavage/lactonization/ intramolecular Friedel-Crafts alkylation, followed by Lewis acid-catalysed cleavage of the acetal protecting groups. image

引用

页数：9

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