Total synthesis of a novel immunosuppressant, myriocin (thermozymocidin, ISP-I), and Z-myriocin.
Myriocin (thermozymocidin, ISP-I), which was known to exhibit several interesting biological properties such as potent immunosuppressive and antifungal activities, and a new analog Z-myriocin were synthesized from 2-deoxy-D-glucose. This synthetic pathway comprises a stereoselective formation of the chiral alpha, alpha-disubstituted amino acid structure in myriocin and Z-myriocin from the isopropylidene six-membered ketone by using a modified Darzen reaction as its key step.
Yoshikawa
M
M
Kyoto Pharmaceutical University, Japan.
Yokokawa
Y
Y
Okuno
Y
Y
Murakami
N
N
D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis; D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D013237:Stereoisomerism
D005229:Fatty Acids, Monounsaturated; D007166:Immunosuppressive Agents; C001996:thermozymocidin