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Synthesis of Ahod Moiety of Ralstonin A Using Amino Acid Schiff Base Ni(II)‐Complex Chemistry
Author(s) -
Oyama Kie,
Han Jianlin,
Moriwaki Hiroki,
Soloshonok Vadim A.,
Konno Hiroyuki
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000077
Subject(s) - chemistry , schiff base , moiety , alkylation , glycine , amino acid , stereochemistry , base (topology) , combinatorial chemistry , organic chemistry , catalysis , biochemistry , mathematical analysis , mathematics
Reported here is the asymmetric synthesis of N ‐Boc‐protected (2 S ,3 S )‐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 α ‐hydroxy functionality. The structure and absolute configuration of (2 S ,3 S )‐ N ‐Boc‐3‐amino‐2‐hydroxyoctadecanoic acid was shown to be identical to that of the naturally occurring compound.