Synthesis of Ahod Moiety of Ralstonin A Using Amino Acid Schiff Base Ni(II)-Complex Chemistry

被引：14

作者：

Oyama, Kie ^{[1
]}

Han, Jianlin ^{[2
]}

Moriwaki, Hiroki ^{[3
]}

Soloshonok, Vadim A. ^{[4
,5
]}

Konno, Hiroyuki ^{[1
]}

机构：

[1] Yamagata Univ, Grad Sch Sci & Engn, Yonezawa, Yamagata 9928510, Japan

[2] Nanjing Forestry Univ, Coll Chem Engn, Nanjing 210037, Peoples R China

[3] Hamari Chem Ltd, Higashi Yodogawa Ku, 1-4-29 Kunijima, Osaka 5330024, Japan

[4] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

[5] Ikerbasque, Basque Fdn Sci, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain

来源：

HELVETICA CHIMICA ACTA | 2020年 / 103卷 / 07期

关键词：

tailor-made amino acids; asymmetric synthesis; Ni(II)-complexes; amino acids; Schiff bases; ralstonin A; DYNAMIC KINETIC RESOLUTION; MICHAEL ADDITION-REACTIONS; ASYMMETRIC-SYNTHESIS; NI(II) COMPLEXES; GLYCINE; HOMOLOGATION; INTERCONVERSION; EFFICIENT; LIGANDS; ALDOL;

D O I：

10.1002/hlca.202000077

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported here is the asymmetric synthesis of N-Boc-protected (2S,3S)-3-amino-2-hydroxyoctadecanoic acid, a component of ralstonin A and ralstoamide A. Key synthetic steps include alkylation of chiral Ni(II) complex of glycine Schiff base, conversion of COOH to keto acid (CO-COOH) and reduction of the carbonyl group to generate alpha-hydroxy functionality. The structure and absolute configuration of (2S,3S)-N-Boc-3-amino-2-hydroxyoctadecanoic acid was shown to be identical to that of the naturally occurring compound.

引用

页数：8