Total Synthesis of Isodesmosine by Stepwise, Regioselective Negishi and Sonogashira Cross‐Coupling Reactions1. Issue 18 (15th May 2015)

• Record Type: Journal Article
• Authors: Koseki, Yohei; Sugimura, Takanori; Ogawa, Keita; Suzuki, Rina; Yamada, Haruka; Suzuki, Noriyuki; Masuyama, Yoshiro; Lin, Yong Y.; Usuki, Toyonobu
• Is Part Of: European journal of organic chemistry. Issue 18(2015)
• Page Start: 4024
• Page End: 4032
• Publication Date: 2015-05-15
• Subjects: Isodesmosine -- Cross‐coupling -- Negishi reaction -- Sonogashira reaction -- Total synthesis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500449
• Languages: English
• ISSNs: 1434-193X

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. Abstract : The total synthesis of isodesmosine, a crosslinking amino acid of elastin and an attractive biomarker of COPD, has been achieved by stepwise and regioselective Negishi and Sonogashira cross‐coupling reactions.