Synthesis of a biomimetic model of calcimycin (A 23187) with a demethylated skeleton

✍ Scribed by Jean-Gabriel Gourcy; Michelle Prudhomme; Gérard Dauphin; Georges Jeminet

• Book ID: 104227025
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 249 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95199-2

✦ Synopsis

The difference in the conformational behaviour of the two arms bearing the coordination sites, as shown by cristallographic studiesl 1, could be of importance for the transporting ability of calcimycin. To examine this point, we undertook the synthesis of a model incorporating an identical overall stereochemistry in its framework, but with lacking methyl groups in positions 11,15,17 and 19 10. While this work was in progress, Nakahara et al.12 achieved the enantiospecific synthesis of tetranormethyl Calcimycin (Scheme 1; RI= NHCH3, R2 = R3 = R4 = R5 = H). This prompted us to report our different synthetic route. PreIiminary results from extraction experiments with calcium and magnesium are also given. Our approach is outlined in Scheme 2. Scheme 2 Br a:(7) b:(8) c:(9)