Total Synthesis of Isodesmosine by Stepwise, Regioselective Negishi and Sonogashira Cross‐Coupling Reactions

Yohei Koseki, Takanori Sugimura, Keita Ogawa, Rina Suzuki, Haruka Yamada, Noriyuki Suzuki, Yoshiro Masuyama, Yong Y. Lin, Toyonobu Usuki

European Journal of Organic Chemistry · 2015 · 18 citations · 34 references

Concepts

Abstract

Abstract 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.

References

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