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Herstellung enantiomerenreiner, α‐alkylierter Lysin‐, Ornithin‐ und Tryptophan‐Derivate
Author(s) -
GanderCoquoz Marlyse,
Seebach Dieter
Publication year - 1988
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.19880710124
Subject(s) - chemistry , alkylation , indole test , tryptophan , electrophile , hydrolysis , lysine , deprotonation , alkaline hydrolysis , stereochemistry , enantiomer , yield (engineering) , amino acid , medicinal chemistry , organic chemistry , biochemistry , catalysis , ion , materials science , metallurgy
Synthesis of Enantiomerically Pure, α‐Alkylated Lysine, Ornithine, and Tryptophan Derivatives The imidazolidinones 9 and 10 as well as the oxazolidinone 18a were prepared in several steps by known methods from lysine and ornithine with an overall yield of ca. 20%. After double deprotonation with LDA, the corresponding dianionic derivatives could be diastereoselectively alkylated with electrophiles (MeI, C 6 H 5 CH 2 Br, C 6 H 5 CHO, CH 3 CHO). Acid hydrolysis led to the two enantiomeric 2‐methyl‐ and 2‐benzyllysines and to the enzyme inhibitor ( S )‐2‐methylornithine. Several α‐alkylated tryptophan derivatives were obtained through alkylation of the heterocycles derived from various amino acids with 1‐( tert ‐butyloxycarbonyl)‐3‐(bromomethyl)indole ( 26 ). Alkaline hydrolysis of the five‐membered auxiliary ring of 30b followed by treatment with HCl afforded ( S )‐2‐methyltryptophan ( 31 ).