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
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页数：9
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