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Total Synthesis of Isodesmosine by Stepwise, Regioselective Negishi and Sonogashira Cross‐Coupling Reactions
Author(s) -
Koseki Yohei,
Sugimura Takanori,
Ogawa Keita,
Suzuki Rina,
Yamada Haruka,
Suzuki Noriyuki,
Masuyama Yoshiro,
Lin Yong Y.,
Usuki Toyonobu
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500449
Subject(s) - negishi coupling , chemistry , sonogashira coupling , regioselectivity , desmosine , palladium , combinatorial chemistry , organic chemistry , amino acid , catalysis , biochemistry
Isodesmosine is a crosslinking pyridinium amino acid of elastin and is an attractive biomarker for the diagnosis of chronic obstructive pulmonary disease (COPD). In this paper, we describe the total synthesis of isodesmosine. The key features of this synthesis are stepwise and regioselective palladium‐catalyzed Negishi and Sonogashira cross‐coupling reactions for efficient introduction of amino acid segments on the pyridine ring.